有机化学双语教学补充材料
王俊儒等编
SECTION A - STRUCTURE AND BONDING
1.Which of the following compounds would have the highest boiling point?
(a)CH3CH2CH2CH3 (b)CH3NH2
(c)CH3OH (d)CH2F2
2.Which of the following alkanes would have the highest boiling point?
3.How are the following compounds related?
(a)isoelectronic species (b)isotopes (c)isomers (d)These compounds are not related at all...they are
totally different.
4.What is the total number of sigma bonds found in the following compound?
(a)8 (b)10 (c)11
(d)15
5.What is the total number of pi bonds found in the following compound?
(a)1 (b)2 (c)3 (d)4
6 All the following compounds are characterized by ionic bonding between a group 1 metal
cation and a tetrahedral anion. Write an appropriate Lewis structure for each anion, remembering to specify
formal charges where they exist.
(a) NaBF4
(b) LiAlH4
(c) K2SO4
(d) Na3PO4
7. The connectivity of carbon oxysulfide（氧硫化碳）is OCS.
(a) Write a Lewis structure for carbon oxysulfide that satisfies the octet rule.
(b) What is the molecular geometry according to VSEPR?
(c) Does carbon oxysulfide have a dipole moment? If so, what is its direction?
8. Peroxides are compounds that contain an O—O bond. Write Lewis formulas for two isomeric peroxides
having the molecular formula C2H6O2. Include all unshared electron pairs.
9. Write a Lewis structure for each of the following organic molecules:
(a) C2H3Cl [vinyl chloride（氯乙烯）: starting material for the preparation of poly(vinyl chloride), or PVC,
plastics]
(b) C2HBrClF3[halothane（三氟溴氯乙烷）: a nonflammable inhalation anesthetic; all three fluorines are
bonded to the same carbon]
(c) C2Cl2F4[Freon （氟利昂）114: formerly used as a refrigerant and as an aerosol propellant; each carbon
bears one chlorine）
SECTION B - ALKANES AND CYCLOALKANES
1.What is the IUPAC name for the following compound?
(a)1,3-pentamethylpropane (b)1,1,3,3-tetramethylbutane
(c)2,4,4-trimethylpentane
(d)2,2,4-trimethylpentane
2.What is the IUPAC name for the following compound?
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(a)dimethylcyclohexane (b)1,3-dimethylcyclohexane
(c)cis-1,3-dimethylcyclohexane (d)trans-1,3-dimethylcyclohexane
3.The most stable conformational isomer of cis-1-bromo-2-chlorocyclohexane will have...
(a)both halide atoms in axial positions. (b)both halide atoms in equatorial positions.
(c)the bromine atom in an axial position and the chlorine atom in an equatorial position.
(d)the bromine atom in an equatorial position and the chlorine atom in an axial position.
4.The most stable conformational isomer of trans-1-ethyl-2-methylcyclo- hexane will be...
5.Which Newman projection shows the most stable conformation of the following compound?
6.Which of the following compounds would yield this energy-rotation diagram?
7.Which of the these compounds represents the major monochlorination isomer formed in the following
reaction?
8.How many dichlorinated isomers can be formed by the halogenation of CH3CH2CH2CH3 with Cl2 in the
presence of light?
(a)2 (b)3 (c)5 (d)6
9. The general molecular formula for alkanes is CnH2n+2. What is the general molecular formula for:
(a) Cycloalkanes
(b) Alkenes
(c) Alkynes
(d) Cyclic hydrocarbons that contain one double bond
10. A certain hydrocarbon has a molecular formula of C5H8. Which of the following is not a structural
possibility for this hydrocarbon?
(a) It is a cycloalkane.
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有机化学双语教学补充材料
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(b) It contains one ring and one double bond.
(c) It contains two double bonds and no rings.
(d) It is an alkyne.
11. Which of the hydrocarbons in each of the following groups are isomers?
(a)
(CH3)3CH
CH3
(b) CH3CCH3
CH3
(C)
CH3
CH2
HC
CCH2CH2C
CCH3
SECTION D - STEREOCHEMISTRY
1.Which of the Fischer projections correctly depicts the following compound?
2.The following stereoisomers are related as...
(a)enantiomers. (b)diastereomers. (c)epimers. (d)identical compounds.
3.Which of the following compounds exhibit optical activity?
4.Determine which of the carbon atoms in the following compounds are chiral. Every carbon atom is a
clickable hot spot so you can get practice recognizing the chiral centers. If the carbon atom is chiral, you will
then be asked to determine the "R" or "S" designation for that atom.
5. What is the major product of the following reaction?
(a)S-2-butanol (b)R-2-butanol (c)a racemic mixture of 2-butanol
(d)the hemiketal of 2-butanone and methanol...2-hydroxy-2-methoxybutane
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6. Give the IUPAC names of each of the following alkanes.
CH3
H
H3C
CH3
CH3
H
H
H
CH3
H
CH2CH(CH3)2
H
H H
H
CH2CH3
C(CH3)3
H
SECTION E - NUCLEOPHILES AND ELECTROPHILES
1 Label the following radicals in the order of their decreasing stability (for example,#6 is the most stable, #1 is
the least stable):
.
A
1) A>B>C
B
C
2). B>A>C
3). C>B>A
B
C
4). B>C>A
2 Reactive in SN2 reactions:
A
1) D>B>C>A
2). D>C>B>A
3). C>D>B>A
D
4). A >B>C> D
3 Reactive in SN1 reactions:
A
1) B>A>D>C
B
C
2). D>C>B>A
3). C>D>B>A
D
4). A >B>C> D
4 Reactivity toward aromatic electrophilic substitution reactions
A
1) B>A>D>C
B
2). A>D>B>C
C
D
3). C>D>B>A
4). A >D>C>B
5. Write the structure of the principal organic product to be expected from the reaction of
1-bromopropane with each of the following:
(a) Sodium iodide in acetone
(b) Sodium acetate (CH3COONa) in acetic acid
(c) Sodium ethoxide in ethanol
(d) Sodium cyanide in dimethyl sulfoxide
(e) Sodium azide in aqueous ethanol
(f) Sodium hydrogen sulfide in ethanol
(g) Sodium methanethiolate (NaSCH3) in ethanol
6. All the reactions of 1-bromopropane in the preceding problem give the product of nucleophilic substitution
in high yield. High yields of substitution products are also obtained in all but one of the analogous reactions
using 2-bromopropane as the substrate. In one case, however, 2-bromopropane is converted to propene,
especially when the reaction is carried out at elevated temperature (about 55℃). Which reactant is most
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effective in converting 2-bromopropane to propene?
SECTION F - REACTIONS AND MECHANISMS
1. Which of the following reactions involves free radical intermediates.
A) CH3CH=CH2 + HBr ----> CH3CHBrCH3
B) CH3CH=CH2 + HBr ----> CH3CH2CH2Br
C) CH3CHO + HCH ----> CH3CH(OH)CN
E)
CH2=CHNMe3+
+ HI ---->
D) CH3CH=CH2 + HOCl ----> CH3CH(OH)CH2Cl
ICH2CH2NMe3+
2. Which of the following carbonyl compounds will be most readily attacked by nucleophiles?
A) C6H5CHO
B) CH3CHO C) HCHO
D) CH3COCH3 E) C6H5COC6H5
3. Which of the following reactions is classed as a nucleophilic aromatic substitution?
A) Sulphonation of benzene
B) Reaction of a protein with dinitrofluorobenzene
C) Reaction of the diazonium cation with phenol
D) The conversion of pyridine to pyrrolidine
E) The hydrolysis of benzyl bromide
4. When ICl adds to cyclohexene in the dark an unstable intermediate is formed.
This is:
A) C6H10I+
B) C6H10I-
C) C6H10Cl+
D) C6H10Cl-
E) C6H10ICl
5. An SN2 reaction involvess:
A) a two-step process. B) a radical intermediate.
C) a carbonium ion intermediate.
D) a one-step, synchronous process.
6. CH3CHO + NH2NH2 ----> CH3CH=N-NH2
Classify the above reaction as
A) nucleophilic substitution
D) electrophilic addition
B) elimination
C) condensation
E) electrophilic substitution
SECTION G - ACID-BASE REACTIONS
1.Which of the following compounds is the strongest Brønsted base?
(a)CH4 (b)NH3 (c)H2O (d)HF
2.What is the major product obtained from the following reaction?
3.Which of the following compounds is the strongest Brønsted base?
(a)H2PO4- (b)HSO4- (c)NO3- (d)CH3COO4.What is the major product obtained from the following reaction sequence?
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理学院应用化学系有机化学教研室
SECTION H- ALKENES AND ALKYNES
1.The best nomenclature for the geometry of the following compound is...
(a)cis- (b)trans- (c)E-
(d)Z-
2.Arrange the following groups in decreasing order of priority for E/Z nomenclature with the highest priority
group listed first.
(a)B>A>C (b)B>C>A (c)A>C>B (d)C>A>B
3.What is the best name for the following compound?
(a)3-methylenehexane (b)2-propyl-1-butene
(c)4-ethyl-4-pentene (d)2-ethyl-1-pentene
4.What is the best name for the following
(a)2-methylcyclohexene
compound?
(b)3-methylhexene
(c)1-methylcyclohex-2-ene
(d)3-methylcyclohexene
+
5.The mechanism of the reaction of propene with H3O will proceed through which of the following
intermediates?
6.The reaction of propene with HBr in the presence of ROOR (peroxide) proceeds through which of the
following intermediates?
7.What is the major product expected from the following reaction?
8.What is the major product expected from the following reaction?
9.What is the major product expected from the following reaction?
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有机化学双语教学补充材料
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10.The mechanism of the reaction of propene with HOCl (Cl2 + H2O) will proceed through which of the
following intermediates?
11.What is the IUPAC name for the following compound?
(a)4-vinyl-2-pentyne (b)4-methylhex-2-yn-5-ene (c)3-methylhex-4-yn-1-ene (d)3-methylhex-1-en-4-yne
12.What is the major product expected from the following reaction?
13.What is the major product expected from the following reaction?
14.What is the major product expected from the following reaction?
15.What is the major product expected from the following reaction?
16. Provide the IUPAC name for each of the following alkynes:
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理学院应用化学系有机化学教研室
(a) CH3CH2CH2C
(b) CH3CH2C
(c) CH3C
CH
CCH3
CCHCH(CH3)2
CH3
(d)
CH2CH2CH2C
CH
17. Write structural formulas for each of the following:
(a) 3,4-Octadiene
(b) (E,E)-3,5-Octadiene
(c) (Z,Z)-1,3-Cyclooctadiene
(d) (Z,Z)-1,4-Cyclooctadiene
(e) (E,E)-1,5-Cyclooctadiene
(f) (2E,4Z,6E)-2,4,6-Octatriene
(g) 5-Allyl-1,3-cyclopentadiene
(h) trans-1,2-Divinylcyclopropane
(i) 2,4-Dimethyl-1,3-pentadiene
18. Give an acceptable IUPAC name for each of the following compounds:
(a) H2C CH(CH2)3CH
CH2
(b)
(c) (H2C CH)3CH
(d)
H
H
Cl
(e) H
H
Cl
H
H
19. Answer the following questions.
(a) What compound of molecular formula C6H10 gives 2,3-dimethylbutane on catalytic hydrogenation over
platinum?
(b) What two compounds of molecular formula C11H20 give 2,2,6,6-tetramethylheptane on catalytic
hydrogenation over platinum?
20. Write structural formulas for all the
(a) Conjugated dienes
(b) Isolated dienes
(c) Cumulated dienes
that give 2,4-dimethylpentane on catalytic hydrogenation.
SECTION I - AROMATIC CHEMISTRY
1.Which of the following is an intermediate in the reaction of benzene with CH3Cl and AlCl3?
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有机化学双语教学补充材料
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2.Which of the following is an intermediate in the reaction of benzene with Br2 and AlBr3?
3.Which of the following reagents would be the best reactants for the following synthesis?
4.Which of the following compounds is aromatic?
5.Which of the following represents the best resonance form for H2C=CHF?
6.Which of the following structures represents the best resonance form for the following compound?
7. Write structural formulas and give the IUPAC names for all the isomers of C6H5C4H9 that contain a
monosubstituted benzene ring.
8. Write a structural formula corresponding to each of the following:
(a) Allylbenzene
(b) (E)-1-Phenyl-1-butene
(c) (Z)-2-Phenyl-2-butene
(d) (R)-1-Phenylethanol
(e) o-Chlorobenzyl alcohol
(f ) p-Chlorophenol
(g) 2-Nitrobenzenecarboxylic ac
(h) p-Diisopropylbenzene
(i) 2,4,6-Tribromoaniline
(j) m-Nitroacetophenone
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(k) 4-Bromo-3-ethylstyrene id
9. Give reagents suitable for carrying out each of the following reactions, and write the major organic products.
If an ortho, para mixture is expected, show both. If the meta isomer is the expected major product, write only
that isomer.
(a) Nitration of benzene
(b) Nitration of the product of part (a)
(c) Bromination of toluene
(d) Bromination of (trifluoromethyl)benzene
(e) Sulfonation of anisole
(f) Sulfonation of acetanilide (C6H5NHCOCH3)
SECTION J-ALDEHYDES AND KETONES
1 What is the IUPAC name of the following compound?
1) 3-methyl-5-heptanone
2) 5-ethyl-3-hexanone
3) 5-methyl-3-heptanone
4) 2-ethyl-4-hexanone
2 Identify the correct IUPAC name of the compound below?
1) 4-benzyl-5-methylhexanal 2) 5-isopropyl-5-phenylbutanal
3) 2-methyl-3-phenylhexanal 4) 5-methyl-4-phenylhexanal
3 Which of the following is an acceptable IUPAC name for the compound below?
1) o-bromo-m-chlorobenzaldehyde
2) 6-bromo-3-chlorobenzaldehyde
3) 2-bromo-5-chlorobenzaldehyde
4) 1-bromo-4-chlorobenzaldehyde
4 Which of the following has the largest Keq for the formation of the hydrate (as shownbelow)?
5 The carbon-oxygen p bond of an aldehyde is formed by overlap of which two orbitals?
1) sp-sp 2) sp2-sp2 3) sp2-2p 4) 2p-2p
6 Which of the reagents below will oxidize a secondary alcohol to a ketone?
1) LiAlH4 2) HIO4 3) K2Cr2O7, H2SO4/H2O 4) HgSO4, H2SO4/H2O
7 Identify the reagents needed to carry out the following conversion.
1) H2/Lindlar Pd followed by H2SO4/H2O
3) H2O, HgSO4/H2SO4
2) O3 followed by H2O
4) LiAlH4 followed by H2O
8 Which one of the following works best as the reaction steps to carry out the conversionbelow?
1) (1) Br2 (2) NaNH2(xs) (3) H2O, HgSO4/H2SO4
2) (1) B2H6/diglyme (2) H2O2, NaOH (3) PCC/CH2Cl2
3) (1) H2O, H2SO4 (2) CrO3/H2SO4
4) (1) CH3CO3H (2) NaOH, H2O
9 Which of the following reagents would carry out the isotopic substitution reaction shownbelow?
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1) 18O2/Ni (cat.) 2) H218O/HCl (cat.) 3) Cr18O3/pyridine 4) 18O3
10 What is the product of the following reaction?
1）3-methylpentane
3-methyl-2-pentanol 3）3-methyl-2-pentene
3-methyl-1-pentyne
11 What is the product of the reaction below?
12 The compound shown to the right is the hemiacetal formed between:
1) propanal and 2-propanol 2) 2-methylpropanal and ethanol
3) acetone and 1-propanol 4) ethanal and 2-methyl-1-propanol
13 What is the product of the reaction of butanal with excess methanol and catalytic sulfuricacid?
1) CH3CH2CH(OCH3)CHO 2) CH3CH2CH2COOCH3
3) CH3CH2CH2CH2OCH3 4) CH3CH2CH2CH(OCH3)2(OCH3)
14 Identify the products of the hydrolysis of the following compound.
15 Which one of the following is not an intermediate in the acid-catalyzed reaction ofbenzaldehyde with 2
equivalents of methanol to give benzaldehyde dimethyl acetal?
16 The compound shown below is the cyclic hemiacetal of:
1)
5-hydroxyheptanal
2)
5-hydroxy-2-heptanone
6-hydroxy-3-heptanone 4) 6-hydroxyheptanal
17 What is the product of the reaction shown?
18 Acid-catalyzed hydrolysis of the cyclic acetal below gives:
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理学院应用化学系有机化学教研室
1) ethanal and 2-chlorocyclohexanol
2) 1,2-ethanediol and 2-chlorocyclohexanol
3) ethanol and 2-chlorocyclohexanol
4) 1,2-ethanediol and 2-chlorocyclohexanone
19 What are the products of the following reaction?
1) cyclohexanone and ethanol
2) cyclohexanone and ethanal
3) 1,2-cyclohexanediol and ethanal
4) 1,2-cyclohexanediol and ethanol
20 The acid-catalyzed reaction of propanal with methanol goes from the hemiacetal to theacetal. This can
mechanistically be thought of as:
1) an addition reaction followed by a substitution reaction.
2) a substitution reaction followed by an addition reaction.
3) an elimination reaction followed by a substitution reaction.
4) an addition reaction followed by an elimination reaction.
21 Which one of the following gives ethanal,CH3CHO,(as one of two products)when added to an aqueous
solution of HCl?
22 Which synthetic method below correctly does the following conversion?
1) (1) Mg, diethyl ether (2) D2O
2) (1) LiAlD4, diethyl ether (2) D2O
3) (1) HOCH2CH2OH, H+ (2) Mg, diethyl ether (3)
D2O (4) H2O, H+
4) (1) HOCH2CH2OH, H+ (2) DCl (3) H2O, H+
23 What is the product of the reaction below?
1) 2-methyl-1-pentene 2) 2-methyl-2-propyloxirane
3) 4-methyl-1-pentene 4) 1-pentene
24 Domiodol,shownbelow,is used medicinally as a mucolytic agent.What are the acidcatalyzed hydrolysis
products of Domiodol?
25 Which of the following reacts with (CH3CH2)2NH to give the compound shown below?
26 What is the product of the following reaction sequence?
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27 Baeyer-Villiger oxidation reaction can use peroxycarboxylic acids to convert ketonds to:
1) carboxylic acids 2) esters.
3) epoxides
4)α-hydroxy ketones
28 Identify the missing reagent for the reaction below.
29 What is the product of the following Baeyer-Villiger oxidation reaction?
30 Which of the following is the product of the reaction between acetone, CH3COCH3,and methylamine,
CH3NH2?
31 Which of the following reacts with methylamine at the fastest rate?
1) 1-pentene
2) pentanal
3) 2-pentanone
4) 3-pentanone
32 Which of the following gives the greatest percentage of hydrate (gen-diol)when dissolved in water?
1) butanal 2) 2,2-dichlorobutanal 3) 3,3-dichlorovutanal
4) 4,4-dichorovutanal
33 Which of the following methods can be used to synthesize
2-methyl-1-hexene,shown above,with no formationof
by-products?
34 Which of the following is the best method to synthesize
2-methyl-3-pentene, shown below,with little or no
by-product formation?
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理学院应用化学系有机化学教研室
35 What is the product of the reaction sequence below?
1) 2-methyl-1-hexene
2) 2,3-dimethyl-2-pentene
3) 2-methyl-2-hexene
4) 3-methyl-1-hexene
36 Propose a mechanism for the following reaction.
37 Propose a mechanism which accounts for the formation of the cyclic compound below.
38. (a) Write structural formulas and provide IUPAC names for all the isomeric aldehydes and ketones that
have the molecular formula C5H10O. Include stereoisomers. (b) Which of the isomers in part (a) yield chiral
alcohols on reaction with sodium borohydride? (c) Which of the isomers in part (a) yield chiral alcohols on
reaction with methylmagnesium iodide?
39. Each of the following aldehydes or ketones is known by a common name. Its substitutive IUPAC name is
provided in parentheses. Write a structural formula for each one.
(a) Chloral (2,2,2-trichloroethanal)
(b) Pivaldehyde (2,2-dimethylpropanal)
(c) Acrolein (2-propenal)
(d) Crotonaldehyde [(E)-2-butenal]
(e) Citral [(E)-3,7-dimethyl-2,6-octadienal]
(f) Diacetone alcohol (4-hydroxy-4-methyl-2-pentanone)
(g) Carvone (5-isopropenyl-2-methyl-2-cyclohexenone)
(h) Biacetyl (2,3-butanedione)
40. The African dwarf crocodile secretes a volatile substance believed to be a sex pheromone. It is a mixture
of two stereoisomers, one of which is shown:
O
H
H
(a) Give the IUPAC name for this compound, including R and S descriptors for its chirality centers.
(b) One component of the scent substance has the S configuration at both chirality centers. How is this
compound related to the one shown? Are the compounds enantiomers, or diastereomers?
41. Predict the product of the reaction of propanal with each of the following:
(a) Lithium aluminum hydride, followed by water
(b) Sodium borohydride, methanol
(c) Hydrogen (nickel catalyst)
(d) Methylmagnesium iodide, followed by dilute acid
(e) Sodium acetylide, followed by dilute acid
(f) Phenyllithium, followed by dilute acid
(g) Methanol containing dissolved hydrogen chloride
(h) Ethylene glycol, p-toluenesulfonic acid, benzene
(i) Aniline (C6H5NH2)
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(j) Dimethylamine, p-toluenesulfonic acid, benzene
(k) Hydroxylamine
(l) Hydrazine
(m) Product of part (l) heated in triethylene glycol with sodium hydroxide
(n) p-Nitrophenylhydrazine
(o) Semicarbazide
42. (a)Write structural formulas for all the noncyclic aldehydes and ketones of molecular formula C4H6O.
(b) Are any of these compounds stereoisomers?
(c) Are any of these compounds chiral?
(d) Which of these are α,β-unsaturated aldehydes or α,β-unsaturated ketones?
(e) Which of these can be prepared by a simple (i.e., not mixed) aldol condensation?
43. The main flavor component of the hazelnut is (2E,5S)-5-methyl-2-hepten-4-one. Write a structural formula
showing its stereochemistry.
44. The simplest α,β-unsaturated aldehyde acrolein is prepared by heating glycerol with an acid catalyst.
Suggest a mechanism for this reaction.
HOCH2CHCH2OH
OH
KHSO4
heat
H2C CHCHO + H2O
45. In each of the following pairs of compounds, choose the one that has the greater enol content, and write
the structure of its enol form:
O
O
(a) (CH3)3CCH
O
or
(CH3)2CHCH
(b) C6H5CC6H5
or
C6H5CH2CCH2C6H5
O
O
O
O
(c) C6H5CCH2CC6H5
(d)
O
or
or
C6H5CH2CCH2C6H5
O
SECTION K - CARBOXYLIC ACIDS AND THEIR DERIVATIVES
1 What is the IUPAC name of the following compound?
1)4-hydroxy-3-methylbutanoic acid
2)3-hydroxy-2-methylbutanoic acid
3)1-hydroxy-2-methylbutanoic acid
4)3-(hydroxymethyl)butanoic acid
2 What is the systematic IUPAC name of the compound below?
1)6-bromo-4-ethylbenzenecarboxylic acid
2)2-bromo-4-ethylbenzenecarboxylic acid
3)ortho-bromo-para-ethylbenzoic acid
4)1-bromo-3-ethylbenzoic acid
3 Rank the following compounds in decreasing order of acidity.
1) B>A>C
2) B>C>A
3) C>B>A
4) C>A>B
4 A mixture of 1-hexanol and hexanoic acid in diethyl ether is shaken with an aqueous sodium bicarbonate
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solution. Which line below correctly describes the major organic species in the two resulting immiscible
solutions?
Ether
sodium bicarbonate solution
1)hexanoic acid
1-hexanol
2)1-hexanol
hexanoic acid
3)sodium hexanoate
1-hexanol
4)1-hexanol
sodium hexanoate
5. The cleansing action of soaps due to the formation of .
1)water insoluble micelles with lipophilic interiors.
2)water soluble micelles with lipophilic interiors.
3)water insoluble micelles with hydrophilic interiors.
4)water soluble micelles with hydrophilic interiors.
6. Which one of the following has the best soap cleansing properties?
1) CH3(CH2)16CO2H 2) CH3CH2CO2H 3) CH3(CH2)16CO2Na 4) CH-3CH2CO2Na
7. Which of the following is the strongest acid?
1) FCH2CO2H
2) ClCH2CO2H
3) BrCH2CO2H
4) ICH2CO2H
8. Which of the following has the largest acid equilibrium constant, Ka?
1) CH3CO2H
2) CH2ClCO2H
3) CHCl2CO2H
4) CCl3CO2H
9. Rank the following three carboxylic acids in order of increasing acidity
A.
4-chlorobutanoic acid
B.
3-chlorobutanoic acid
C.
2-chlorobutanoic acid
1)A<B<C
2) A<C<B
3) C<A<B
4) C<B<A
10 Which of the following has the largest acid equilibrium constant, Ka?
1)benzoic acid
2)ortho-nitrobenzoic acid
3)para-methylbenzoic acid (para-toluic acid)
4)para-methoxybenzoic acid
11. what is the product of the following sequence of reactions?
1)(CH3)2CHCH2CH2NH2
2)(CH3)2C=CHCO2H
3)(CH3)2CHCHBrCO2H
4)(CH3)2CHCH2CO2H
12. What is the product of the reaction shown below?
13. Which of the following is not a good method to make
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有机化学双语教学补充材料
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2,2-dimethylpropanoic acid?
14. Reaction of acetic acid, CH3CO2H, with isotopically labeled CH318OH and catalyticsulfuric acid gives:
15. Which of the product of reaction sequence below?
16. Acetic acid is mixed with isotopically labeled water, H218O, and a small amounthydrochloric acid. Which of
the following results of 18O incorporation would beexpected?
17. Which of the following is the tetrahedral intermediate in the acid-catalyzed Fischer esterification reaction
of acetic acid, CH3CO2H, and ethanol,
CH3CH2OH?
18. What is the product of the reaction
below?
1)2,3-dibromobutanoic acid
2)3-chlorobutanoic acid
3)2-bromobutanoic acid
4)2-chlorobutanoic acid
19. Identify the lactone formed by following hydroxy
carboxylic acid.
20. Which structure below is the hydroxy acid which
corresponds to the following lactone.
21. Which of the following undergo decarboxylation upon heating?
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理学院应用化学系有机化学教研室
1)A and D
2)A and C
3)B and C
4)C and D
22 What is the product of the thermal decarboxylation of dimethylpropanedioic acid?
1)propanoic acid
2)2-methylpropanoic acid
3)2,2-dimethylpropanoic acid
4)acetic acid
23. What is the product of the reaction shown below?
24. Which of the following is the enol intermediate in the thermal decarboxylation ofmethylpropanedioic acid,
CH3CH(CO2H)2?
25. Which one of the following compounds undergoes decarboxylation upon heating?
26. What is the product of the reaction sequence below?
27. Only one of the reaction sequences below can carry out the following transformation. Identify which
reaction sequence it is.
1) (1) Mg/diethyl ether (2) CO2 (3) H2O, H+
(4) CH3O-Na+
2) (1) NaOH (2) Mg/diethyl ether (3) CO2
(4) H2O, H+ (5) CH3I
3) (1) CH3O-Na+ (2) Mg/diethyl ether (3) CO2 (4) H2O, H+
4) (1) CH3O-Na+ (2) KCN, DMSO
(3) H2O, H2SO4, heat
28. Many carboxylic acids are much better known by their common names than by their systematic names.
Some of these follow. Provide a structural formula for each one on the basis of its systematic name.
(a) 2-Hydroxypropanoic acid [better known as lactic acid（乳酸）, it is found in sour milk and is formed in
18
有机化学双语教学补充材料
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the muscles during exercise]
(b) 2-Hydroxy-2-phenylethanoic acid [also known as mandelic acid（扁桃酸；苦杏仁酸), it is obtained from
plums, peaches, and other fruits]
(c) Tetradecanoic acid[also known as myristic acid（肉豆蔻酸）, it can be obtained from a variety of fats]
(d) 10-Undecenoic acid (also called undecylenic acid, it is used, in combination with its zinc salt, to treat
fungal infections such as athlete’s foot)
(e) 3,5-Dihydroxy-3-methylpentanoic acid [also called mevalonic acid（甲羟戊酸）, it is an important
intermediate in the biosynthesis of terpenes and steroids]
(f) (E)-2-Methyl-2-butenoic acid [also known as tiglic acid（巴豆酸）, it is a constituent of various natural
oils]
(g) 2-Hydroxybutanedioic acid [also known as malic acid（苹果酸）, it is found in apples and other Fruits]
(h) 2-Hydroxy-1,2,3-propanetricarboxylic acid [better known as citric acid（柠檬酸）, it contributes to the
tart taste of citrus fruits]
(i) 2-(p-Isobutylphenyl)propanoic acid [an antiinflammatory drug better known as
Ibuprofen（布洛芬）]
(j) o-Hydroxybenzenecarboxylic acid [better known as salicylic acid（水杨酸）, it is obtained from willow
bark]
29. Give an acceptable IUPAC name for each of the following:
(a) CH3(CH2)6COOH
(b) CH3(CH2)6COOK
(c) H2C
(d)
CH(CH2)5CO2H
H3C
(CH2)4CO2H
C
H
C
H
CH2CH3
(f)
(e) HO2C(CH2)6CO2H
CH(CH2)4CO2H
30. Rank the compounds in each of the following groups in order of decreasing acidity:
(a) Acetic acid, ethane, ethanol
(b) Benzene, benzoic acid, benzyl alcohol
(c) Propanedial, 1,3-propanediol, propanedioic acid, propanoic acid
(d) Acetic acid,
ethanol,
trifluoroacetic acid,
2,2,2-trifluoroethanol, trifluoromethanesulfonic acid
(CF3SO2OH)
(e) Cyclopentanecarboxylic acid, 2,4-pentanedione, cyclopentanone, cyclopentene
31. Identify the more acidic compound in each of the following pairs:
(a) CF3CH2CO2H
or
(b) CH3CH2CH2CO2H
CF3CH2CH2CO2H
or
CH3C CCO2H
CO2H
(c)
CO2H
or
32. Write a structural formula for each of the following compounds:
(a) m-Chlorobenzoyl chloride
(b) Trifluoroacetic anhydride
(c) cis-1,2-Cyclopropanedicarboxylic anhydride
(d) Ethyl cycloheptanecarboxylate
(e) 1-Phenylethyl acetate
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理学院应用化学系有机化学教研室
(f) 2-Phenylethyl acetate
(g) p-Ethylbenzamide
(h) N-Ethylbenzamide
(i) 2-Methylhexanenitrile
SECTION L – HALIDES
ARYL HALIDES
1 Which of the following has the weakest carbon-chlorine bond?
2 Which compound in each of the following pairs is the most reactive to the conditions indicated?
1) A and C
2) A and D
3) B and C
4) B and D
3 Which of the following reacts at the fastest rate with potassium methoxide (KOCH3) inmethanol?
1)
fluorobenzene
2)
4-nitrofluorobenzene
3)
2,4-dinitrofluorobenzene
4)
2,4,6-trinitrofluorobenzene
4 Which of the following reacts at the fastest rate with potassium methoxide (KOCH3) in methanol?
1)
fluorobenzene
2)
p-nitrofluorobenzene
3)
p-fluorotoluene
4)
p-bromofluorobenzene
5 Which of the following is the kinetic rate equation for the addition-eliminationmechanism of nucleophilic
aromatic substitution?
1)
rate = k[aryl haldie]]
2)
rate = k[nucleophile]
3)
rate = k[aryl halide][nucleophile]
4)
rate = k[aryl halide][nucleophile]2
6 Which of the following is not a resonance form of the intermediate in the nucleophilicaddition of hydroxide
ion to para-fluoronitrobenzene?
7 Which chlorine is most susceptible to nucleophilic substitution with NaOCH3 inmethanol?
1) #1 2) #2 3) #1 and #2 are equally susceptible 4) no
possible
8 What is the product of the following reaction?
20
substitution
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有机化学双语教学补充材料
1)
N,N-dimethylaniline
2)
para-chloro-N,N-dimethylaniline
3)
phenyllithium (C6H5Li)
4)
meta-chloro-N,N-dimethylaniline
王俊儒等编
9 Which one of the reagents readily reacts with bromobenzene?
1)
NaOCH2CH3 at 250C
2)
NaCN/DMSO at 250C
3)
NaNH2/NH3 at -330C
4)
(CH3)2NH at 250C
10 Which of the following would work best for the synthesis of the ether shown below?
11 Carbon-14 labelled chlorobenzene is reacted with sodium amide in ammonia as shownbelow. Which of the
following depicts the carbon-14 label in the product(s)?
12 Identify the product(s) of the following reaction.CH3Cl NaNH2, NH3 -33oCfrom the reaction shown below?
1)
only ortho-methylaniline
2)
ortho-methtylaniline and meta-methyaniline
3)
meta-methylaniline and para-methyaniline
4)
ortho-methylaniline and para-methyaniline
13 Which of the following best estimates the percentages of the three
isomeric methylanilines from the reaction shown below?
ortho-methylaniline
meta-methyaniline
para-methyaniline
1)
33%
33%
33%
2)
40%
40%
20%
3)
0%
50%
50%
4)
0%
66%
33%
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理学院应用化学系有机化学教研室
14 Which of the following is a key intermediate in the reaction shown below?
15 Identify the diene required for the synthesis shown below.Mg, THF ?
16 Assume that the following reaction goes by the elimination-addition mechanism fornucleophilic aromatic
substitution. Based on that, how many isomeric naphthylamines areexpected in the following reaction?
1)
only
a
sing
le
prod
uct
2)
two
3)
three
4) four
17 Which of the following best estimates the percentages of the three isomericdeuterated anilines from the
reaction shown right?
18 Which of the following is (are) true concerning the intermediate benzyne?
A. Benzyne is aromatic.
B. All the hydrogens of benzyne are equivalent and indistinguishable
C. The benzyne molecule has strain energy.
1) only A
2) only C
3) A and C
4) B and C
19 Which of the following is (are) true concerning the intermediate in the addition-eliminationmechanism of
the reaction below?
A. The intermediate is aromatic
B. The intermediate is a resonance stabilized anion
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C. Electron withdrawing groups in the benzene ring stabilize the intermediate
1) only A
2)only B
3)A and C
4)B and C
20 Which one of the following has the fastest rate of reaction with sodium ethoxide ,NaOCH2CH3,at 25℃?
1)
para-fluoronitrobenzene
2)
para-chloromitrobenzene
3)
para-bromonitrobenzene
4)
para-iodonitrobenzene
21 Arrange the following compounds in order of increasing reactivity with sodium methoxide,NaOCH3?
1) A<B<C
2) A<C<B
3) B<A<C
4) C<B<A
22 Which position on the potential energy diagram corresponds to the species shown for thereaction of
para-fluoro(trifluoromethyl)benzene with sodium methoxide?
1)A
2)B
3)C
4)D
23 Which of the following is the product from the reaction sequence shown below?
24. Write a structural formula for each of the following:
(a) m-Chlorotoluene
(b) 2,6-Dibromoanisole
(c) p-Fluorostyrene
(d) 4,4-Diiodobiphenyl
(e) 2-Bromo-1-chloro-4-nitrobenzene
(f) 1-Chloro-1-phenylethane
(g) p-Bromobenzyl chloride
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理学院应用化学系有机化学教研室
(h) 2-Chloronaphthalene
(i) 1,8-Dichloronaphthalene
(j) 9-Fluorophenanthrene
25. Identify the major organic product of each of the following reactions. If two regioisomers are formed in
appreciable amounts, show them both
(a) Chlorobenzene
+
acetylchloride
(b) Bromobenzene + magnesium
AlCl3
diethyl ether
(c) Product of part (b) + dilute hydrochloric acid
(d) Iodobenzene + lithium
diethyl ether
(e) Bromobenzene + sodium amide liquid ammonia, -33℃
(f) P-Bromotoluene + sodium amide
liquid ammonia,-33℃
(g) 1-Bromo-4-nitrobenzene + ammonia
(h) P-Bromobenzyl bromide +sodium cyanide
(i) P-Chlorobenzenediazonium chloride +N,N-dimethyaniline
(j) Hexafluorobenzene + sodium hydrogen sulfide
SECTION M - ALCOHOLS, PHENOLS, AND THIOLS
1 Which of the following cannot be made by the reduction of a ketone or aldehyde with NaBH4 in methanol?
1) 1-butanol 2) 2-butanol 3) 2-methyl-1-propanol 4) 2-methyl-2-propanol
2 An alcohol has the same oxidation state as a(n):
1) ketone 2) alkene 3) organolithium compound 4) alkyl halide
3 In general, the reduction of a ketone to an alcohol can be accomplished by all of the following except one.
Which one will not reduce a ketone?
1) H2/Pt
2) HIO4 3) LiAlH4 4)
NaBH4
4 What is the product of the following
reaction?
5 Which of the following is not readily oxidized by K2Cr2O7 in H2SO4/H2O?
1) n-butyl alcohol 2) sec-butyl alcohol 3) isobutyl alcohol 4) tert-butyl alcohol
6 In general, which one of the functional groups below does not react with LiAlH4?
1) esters 2) ketones 3) ethers 4) carboxylic acids
7 Give the product of the following reaction.
8 Which of the following reagents would be used to
carry
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有机化学双语教学补充材料
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out the transformation shown below?
1) NaBH4
2) LiAlH4
3) H2/Pt
4) PCC/CH2Cl2
9 The reaction of a Grignard reagent with ethylene oxide followed by dilute acid gives:
1) a primary alcohol
2) a secondary alcohol 3) a tertiary alcohol
4) methanol
10 What is the product of the following reaction?
1)
CH3CH=O
2)
meso-2,3-butanediol
3)racemic
(2R,3R)
and
(2S,3S)-2,3-butanediol
4)
cis-2,3-epoxybutane
11 Consider the conversion of 1-butanol to each of the compounds shown below. In which conversion is an
oxidizing agent needed?
12 Which of the following syntheses gives 3-methyl-1-hexanol?
13 Identify the reagent needed to carry out the following conversion.
1) K2Cr2O7, H2SO4/H2O 2) PCC/CH2Cl2 3) HIO4
4) OsO4, (CH3)3COOH, (CH3)3COH, OH-
14 Which one of the following diols would cleave into two fragments with HIO4?
1) 1,3-hexanediol 2) 2,4-hexanediol
15 Consider the structure of the
1) -1
2) 0
3) +1
AlH4-
3) 3,4-hexanediol 4) 1,6-hexanediol
ion. The formal charge of Al is:
4) +3
16 As a reducing agent, NaBH4 donates a(n) __________ to a ketone or aldehyde.
1) proton 2) hydrogen atom 3) hydride ion 4) hydrogen molecule
17 Which of the following best describes the role of the coenzyme NAD+ (nicotinamideadenine dinucleotide)
in biological chemistry?
1) It reduces other species.
2) It oxidizes other species.
3) It catalyzes oxidation-reduction reactions.
4) It inhibits oxidation-reduction reactions.
18 What is the product of the synthetic sequence below?
19 Compound A, C6H12O, is readily oxidized with K2Cr2O7 in H2SO4/H2O to givecompound B, C6H10O.
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理学院应用化学系有机化学教研室
Compound B has four peaks in its C13 NMR (broadbanddecoupling). Which one of the following fits the
data for compund A?
20 What is the final product of the following reactions?
1) 2,3-dimethyl-3-pentanol
2) 2,3-diemthyl-2-pentanol
3) 2,4-dimethyl-3-pentanol
4) 2,2-dimethyl-3-pentanol
21 Which of the following is the ester formed between methanol and nitric acid, HNO3?
22 The tertiary alcohol below was reacted with PCC in CH2Cl2 and gave a product,C12H12O. The product had
a strong absorption in the IR spectrum at 1700 cm-1. Predic twhich of the following is the product. (note:
PCC is pyridinium chlorochromate,[C5H5NH+][ClCrO3-])
23 What is the product of the reaction below?
1) CH3CH2COOOCCH3
2) CH3COOCH2CH2CH3
3) CH3CH2CH2COCH3
4) CH3CH2COOCH2CH3
24 Which of the following reagents will convert cyclohexene into cis-1,2-cyclohexanediol?
1) OsO4, (CH3)3COOH, (CH3)3COH, OH3) O3 followed by Zn/H2O
2) HIO4
4) CH3CO3H (peroxyacetic acid)
25 In which of the following forms does nicotinamide adenine dinucleotide have an aromatic pyridine ring?
1) NADH
2) NAD+
3) both NADH and NAD+ 4) neither NADH or NAD+
26 Which of the synthetic procedures below would carry out the following transformation?
1) LiAlH4 followed by H2SO4/heat
2) O3 followed by (CH3)2S
3) PCC/CH2Cl2 followed by HIO4
4) NaBH4/methanol followed by HIO4
1) LiAlH4, diethyl ether2) H2O
27 The alcohol product(s) of the reduction of 2-methyl-3-pentanone with LiAlH4 is (are):
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有机化学双语教学补充材料
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1) a single enantiomer.2) a racemic mixture.3) two diastereomers.4) two constitutional isomers.
28 What is the product of the following reaction sequence?
29 Which one of the following reaction steps work best to carryout the transformationshown below?
30. Write chemical equations, showing all necessary reagents, for the preparation of 1-butanol by each of the
following methods:
(a) Hydroboration–oxidation of an alkene
(b) Use of a Grignard reagent
(c) Use of a Grignard reagent in a way different from part (b)
(d) Reduction of a carboxylic acid
(e) Reduction of a methyl ester
(f) Reduction of a butyl ester
(g) Hydrogenation of an aldehyde
(h) Reduction with sodium borohydride
31. Write chemical equations, showing all necessary reagents, for the preparation of 2-butanol by each of the
following methods:
(a) Hydroboration–oxidation of an alkene
(b) Use of a Grignard reagent
(c) Use of a Grignard reagent different from that used in part (b)
(d–f) Three different methods for reducing a ketone
32. Write chemical equations, showing all necessary reagents, for the preparation of tert-butyl alcohol by:
(a) Reaction of a Grignard reagent with a ketone
(b) Reaction of a Grignard reagent with an ester of the type RCOOCH3
33. Which of the isomeric C5H12O alcohols can be prepared by lithium aluminum hydride
reduction of:
(a) An aldehyde
(b) A ketone
(c) A carboxylic acid
(d) An ester of the type RCOOCH3
34. Evaluate the feasibility of the route
RH
Br2
light or heat
RBr
KOH
ROH
as a method for preparing
(a) 1-Butanol from butane
(b) 2-Methyl-2-propanol from 2-methylpropane
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理学院应用化学系有机化学教研室
(c) Benzyl alcohol from toluene
(d) (R)-1-Phenylethanol from ethylbenzene
35. Sorbitol is a sweetener often substituted for cane sugar, because it is better tolerated by diabetics. It is
also an intermediate in the commercial synthesis of vitamin C. Sorbitol is prepared by high-pressure
hydrogenation of glucose over a nickel catalyst. What is the structure (including stereochemistry) of sorbitol?
36. The IUPAC rules permit the use of common names for a number of familiar phenols and aryl ethers.
These common names are listed here along with their systematic names. Write the structure of each
compound.
(a) Vanillin（香草醛；香兰素） (4-hydroxy-3-methoxybenzaldehyde): a component of vanilla bean oil, which
contributes to its characteristic flavor
(b) Thymol（麝香草酚）(2-isopropyl-5-methylphenol): obtained from oil of thyme
(c) Carvacrol（香芹酚；香荆芥酚）(5-isopropyl-2-methylphenol): present in oil of thyme and marjoram
(d) Eugenol（丁子香酚）(4-allyl-2-methoxyphenol): obtained from oil of cloves
(e) Gallic acid（五倍子酸；没食子酸） (3,4,5-trihydroxybenzoic acid): prepared by hydrolysis of tannins
derived from plants
(f) Salicyl alcohol（水杨醇）(o-hydroxybenzyl alcohol): obtained from bark of poplar and willow trees
37. Name each of the following compounds:
OH
OH
(a)
Cl
(b)
(c) HO
CH2CH3
NO2
H3C
CH2
NO2
CH2CH3
OCH3
CH3
Cl
OOCCl3
(e)
(d)
CH(CH3)2
Cl
38. Write a balanced chemical equation for each of the following reactions:
(a) Phenol+sodium hydroxide
(b) Product of part (a) + ethyl bromide
(c) Product of part (a) +butyl p-toluenesulfonate
(d) Product of part (a) +acetic anhydride
(e) o-Cresol+benzoyl chloride
(f) m-Cresol+ ethylene oxide
(g) 2,6-Dichlorophenol+bromine
(h) p-Cresol+excess aqueous bromine
(i) Isopropyl phenyl ether+ excess hydrogen bromide+ heat
39. Which phenol in each of the following pairs is more acidic? Justify your choice.
(a) 2,4,6-Trimethylphenol or 2,4,6-trinitrophenol
(b) 2,6-Dichlorophenol or 3,5-dichlorophenol
(c) 3-Nitrophenol or 4-nitrophenol
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有机化学双语教学补充材料
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SECTION O - AMINES AND NITRILES
1 What is an acceptable name of the following compound?
CH3CH2CH2CH2NHCH3
1) N-methylbutylamine
3) N-butylmethylamine
2) 1-methyl-1-butylamine
4) 2-pentylamine
2 What is the IUPAC name of the following compound?
1)
2-methyl-4-hexanamine
2)
2-methyl-4-aminohexane
3)
5-methyl-3-hexanamine
4)
5-methyl-3-aminohexane
3 Which of the following is the correct IUPAC name of the compound shown below?
1)
1,2-dichloro-4-(N,N-dimethyl)aniline
2)
dimethyl-(3,4-dichlorophenyl0amine
3)
3,4-dichloro-N,N-dimethylaniline
4)
N,N-dimethylamino-3,4-dichlorobenzene
4 Which one of the following is ethyl 4-(dimethylamino)butanoate?
1)
(CH3NH)2CHCH2CH2CO2CH2CH3
2)
H2NCH2CCH2CO2CH2CH3
3)
(CH3)2CCH2CH2CO2CH2CH3
4)
(CH3)2NCH2CH2CH2CO2CH2CH3CH3CH3NH2
5 Among the isomeric C4H11N amines below, the one with the lowest boiling point is:
1) CH3CH2CH2CH2NH2
2) (CH3CH2)2NH
3) (CH3)2CHNHCH3
6 Rank the following three compounds in order of decreasing basicity.
1) A>B>C
2) B>A>C
3) C>B>A
4) C>A>B
7 Rank the following three compounds in order of decreasing acidity.
1) B>C>A
2) B>A>C
3) C>A>B
4) C>B>A
8 In the following two-phase reaction, the catalyst works by:
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4) (CH3)2NCH2CH3
理学院应用化学系有机化学教研室
1)transferring CN- from the aqueous phase to the organic phase containing C6H5CH2Br.
2)transferring C6H5CH2Br from the organic phase to the aqueous phase containing CN-.
3)removing Br- from the organic phase to the aqueous phase.
4)removing K+ from the organic phase to make cyanide ion more nucleophilic.
9 Which one of the compounds showing right is not a resonance form of para-aminobenzaldehyde?
10 To convert a nitrile to a primary amine you must:
1)hydrolyze it with water.
2)oxidize it with chromic acid.
3)reduce it with hydrogen or lithium aluminum hydride.
4)substitute it with an alkyl halide.
11 Which one of the compounds showing right is the strongest base?
12 Which of the following is the product of the reaction shown below?
1) (CH3)2CHCH2CH2NHNH2
2) (CH3)2CHCH2CH2NH2
3) [(CH3)2CHCH2CH2]2NH
4) (CH3)2CHCH2CH2CONH2
13 Which pair of reagents would be used to make the following amine by reductiveamination?
1)methylamine and 2-methylbutanoec acid
2)methylamine and 2-methylbutanal
3)ammonia and 3-methyl-2-pentaqnone
4)dimethylamine and 2-butanone
14 Which of the following reagents can convert cyclohexanone to N-ethylcyclohexylmine as shown below?
1)CH3CH2NH2 and H2/Pt
2)CH3CH2Br and NH3
3)LiAlH4 followed by H2O and then CH3CH2Br
4)CH3CH=O and NH3
15 Which one of the following compounds gives propylamine, CH3CH2CH2NH2, upon hydrolysis?
16 Rank the three compounds showing right in decreasing order of basicity.
1) C>A>B
2) C>B>A
3) B>A>C
4) B>C>A
17 Which one of the following does not give N-ethylcyclopentylamine as the major product?
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18 Which one of the following synthetic routes gives the best yield of meta-bromoanilinestarting with
benzene?
19 Which one of the following amines gives an N-nitrosoamine on treatment with nitrousacid, HNO2?
1)2,4-dimethylaniline
2)3,5-dimethyaniline
3)N,4-dimethylaniline
4)N,N-dimethylaniline
20 What is the product of the following reaction?
1)3,5-dimethyl-4-nitrophenol
2)meta-xylene(meta-dimethybenzene)
3)1,3-dimethyl-5-nitrobenzene
4)3,5-dimethylphenol
21 Which of the following is the product of the reaction sequence shown below?
1)meta-bromochlorobenzene
2)1,3,5-tribromobenzene
3)1,3-dibromo-5-chlorobenzene
4)mixture of ortho and para-bromochlorobenzene
22 Which of the following would be the starting reagents needed to make the azocompound shown below?
23 Reaction of an N,N-dialkylaniline with nitrous acid yields:
1)a diazonium salt
2)a para-nitroso compound
3)an N-nitroso compound
4)an azo compound
24 What is the product of the reaction series shown below?
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理学院应用化学系有机化学教研室
25 What is the major product of the reaction sequence below?
1)CH3CH2CH2CH=CH2
2)CH3CH2CH=CHCH3
3)CH3CH2CH2CHCH3
4)CH3CH2CH=CCH3OHNH2
26 Which one of the following forms a diazonium ion on being treated with NaNO2 inaqueous HCl?
1) para-nitrotoluene 2) ethylamine. 3) N,N-dimethylaniline. 4) triethylamine
SPECIAL TOPIC : BIOMOLECULES
P-I
CARBOHYDRATES(SAACHRIDES)
1 What are the configurations of carbon atoms 2 and 3, respectively, of D-threose, shownbelow?
1) R,R
2) R,S
3) S,R
4) S,S
2 How many stereoisomeric aldohexoses are there?
1) four
2) eight
3) sixteen
4) eighteen
3 Which one of the following is not true concerning D-glucose.
1) D-Glucose is a reducing sugar.
2) D-Glucose readily forms cyclic hemiacetals.
3) D-Glucose is optically active.
4) D-Glucose is a ketose.
4 Which one of the following is ?
5 The major form of D-glucose in aqueous
solution is:
1) the open-chain form
2) α-glucopyranose
3) β-D-glucopyranose .
4) β-D-glucofuranose.
6 Which one of the following is not true
concerning
sucrose?
1) Sucrose is a disaccharide.
2) Sucrose is a reducing sugar.
3) Acid-catalyzed hydrolysis of sucrose gives D-glucose and D-fructose.
4) Sucrose does not undergo mutarotation.
7 What is the relationship between open-chain forms of D-glucose and D-altrose?
1) enantiomers
2) diastereomers
3) constitutional isomers
4) different conformations of the same compound
8 Which of the following is the open-chain form of the pyranose structure shown below?
32
有机化学双语教学补充材料
王俊儒等编
9 Theαandβforms of D-glucopyranose can be described as:
1) constitutional isomers
2) enantiomers
3) different conformations of the same compound
4) anomers
10 Which one of the following disaccharides does not undergo mutarotation?
1) sucrose
2) maltose
3) lactose
4) cellobiose
11 Identify the β-pyranose form of D-gulose.
D-gulose
12 The α- and β-pyranose forms of D-glucose
interconvert by:
1)
"ring-flipping" between the two chair conformations.
2)
ring-opening and ring-closing through the open-chain aldehyde form.
3)
epimerization through the enol tautomer.
4)
SN2 inversion with nucleophilic hydroxide ion.
13 Which of the following statements is (are) true concerning the equilibrium between theα-and β-pyranose
forms of D-glucose?
A. The interconversion is acid-catalyzed.
B. Both anomers are equally stable.
C. Both anomers are optically active.
1) only C
2) B and C
3) A and C
4) A, B, and C
14 Which one of the following disaccharides is obtained from the partial hydrolysis of starch?
1) sucrose
2) maltose
3) lactose
4) cellobiose
15 A disaccharide is determined to be a nonreducing sugar. Acid-catalyzed hydrolysis of the disaccharide
gives only D-glucose.What information does this tell you about how the two glucose unite are linked in
the disaccharide?
1) Each of the two glucose units are linked C-1 to C-1.
2) One of the glucose units uses C-1 and it links to theother unit which uses either C-2, C-3, C-4, or C-6.
3) Each of the two glucose units are linked via any carbons except for C-1.
4) The two units must both have βlinkages.
16 Which one of the following polysaccharides has all β(1,4) glycosidic linkages?
1) amylose
2) glycogen
3) cellulose
17 Identify the anomeric carbon in the following carbohydrate.
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4) amylopectine
理学院应用化学系有机化学教研室
18 The principal difference between amylose (from starch) and cellulose is:
1) amylose has exclusively α(1,4)-linked glucose and cellulose hasexclusively β(1,4)-linked glucose.
2) amylose has exclusively α(1,6)-linked glucose and cellulose hasexclusively β(1,4)-linked glucose.
3) amylose has α(1,4)-linked glucose with α(1,6) branches and cellulose hasexclusively β(1,4)-linked glucose.
4) amylose has exclusively α(1,4)-linked glucose and cellulose hasβ(1,4)-linked glucose with α-(1,6)
branches.
19 Which one of the following is most similar to glycogen in terms of how glucose units arelinked?
1) amylose
2) amylopectin
3) cellulose
4) cellobiose
20 Which one of the following gives an optically inactive compound when reacted withsodium borohydride,
NaBH4?
21 The following series of reactions was done on a monosaccharide. What information doesthis give about
the monosaccharide?
1) The monosaccharide was in the open-chain form.
2) The monosaccharide was in the furanose form.
3) The monosaccharide was in the pyranose form.
4) The monosacchride was in the α-anomer form.
22 The α- and β-pyrnaose forms of D-glucose can be described as:
1) cyclic acetals formed between the aldehyde and the hydroxy group on carbon-5.
2) cyclic hemiacetals formed between the aldehyde and the hydroxy group on carbon-5.
3) cyclic acetals formed between the aldehyde and the hydroxy group on carbon-6.
4) cyclic hemiacetals formed between the aldehyde and the hydroxy group on carbon-6.
23 Sucrose is a nonreducing sugar, giving a negative test with Benedict's solution. Thismeans:
1)
C-1 of glucose is linked to C-1 of fructose.
2)
C-1 of glucose is linked to C-2 of fructose.
3)
C-4 of glucose is linked to C-1 of fructose.
4)
C-6 of glucose is linked to C-2 of fructose.
24 Which ome of the following is L-(-)-glucose?
25 How would the glycosidic linkage indicated by the arrow be described for the following disaccharide?
1) α(1,5)
2) α(1,6)
3) α(2,6)
4) β(1,6)
34
有机化学双语教学补充材料
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26. Refer to the Fischer projection of D-(+)-xylose and give structural formulas for
(a) (-)-Xylose (Fischer projection)
(b) Xylitol
H
HO
H
(c) β-D-Xylopyranose
(d) α-L-Xylofuranose
(e) Methyl α-L-xylofuranoside
CHO
OH
H
OH
CH2OH
(f) D-Xylonic acid (open-chain Fischer projection)
D-(+)-xylose
(g)δ -Lactone of D-xylonic acid
(h) γ -Lactone of D-xylonic acid
(i) Xylaric acid (open-chain Fischer projection)
SPECIAL TOPIC : BIOMOLECULES
P-II AMINO ACIDS, PEPTIDES, AND PROTEINS
1 The Fischer projection shown below denotes a ______ amino acid which has
the
_____configuration.
1) D, S
3) L, S
2) D, R
4) L, R
2 What is the total number of different tripeptides which can result from three differentL-amino acids?
1) three
2) four
3) six
4) nine
3 What is the total number of different tripeptides which can result from two L-alanines andone L-serine
amino acids?
1) only one
3) three
2) two
4) six
4 The pKa's of the acidic hydrogens of lysine are shown below. What is the isoelectric pointof lysine?
1) 2.18
2) 5.56
3) 6.36
4) 9.74
5 What is the net charge on L-aspartic acid (R=-CH2CO2H) at
a pH of
11.0?
1) +1
2) +2
3) -1
4) -2
6 In the following table which column has the isoelectric points (pI) correctly matched with the amino acids on
the left? (Note: The side chains are given for each.)
1)
2)
3)
4)
alanine (R = -CH3)
10.0
3.0
3.0
6.0
aspartic acid (R = -CH2CO2H)
6.0
10.0
6.0
3.0
lysine (R = CH2CH2CH2CH2NH2)
3.0
6.0
10.0
10.0
7 In strongly acidic solution L-lysine is primarily a dication as shown below. As the pH israised, which proton
is lost to form the monocation?
8 Linus Pauling is credited with describing the α-helix
polypeptide.
Theα-helix
is
an
example
of
a
polypeptide's:
1)
primary structure
2)
secondary structure
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structure of a
理学院应用化学系有机化学教研室
3)
tertiary structure
4)
quaternary structure
9 What is the net charge on the dipeptide lys-asp at a pH of 1.0?
aspartic acid (R = -CH2CO2H)
lysine (R = CH2CH2CH2CH2NH2)
1) +1
2) +2
3) +3
4) +4
10 A pentapeptide was found to contain the amino acids ala, gly, met, phe, and ser. Partialhydrolysis of the
pentapeptide gave the dipeptides gly-ser, met-phe, ala-gly, and ser-met.What is the sequence of the
pentapeptide?
1)
gly-ser-met-phe-ala
2)
gly-ser-met-ala-phe
3)
ala-gly-ser-phe-met
4)
ala-gly-ser-met-phe
11 The peptide linkage in proteins and peptides is planar and has restricted rotation about the carbon-nitrogen
because
1)
the peptide bond has partial double bond character.
2)
hydrogen bonding requires a planar arrangement and restricts bond rotation.
3)
the steric hindrance of the large side chains.
4)
the carbonyl is predominately in the enol form.
12 Which of the following is the DNP derivative obtained from
the
reaction sequence shownbelow?
13 The pKa's of the acidic hydrogens for aspartic acid are
shown
below.
What
is
theisoelectric point of aspartic
acid?
1) 2.77
2) 3.65
3) 5.74
4) 6.62
14 Complete hydrolysis of a nonapeptide gave 3 ala, 2 phe, 2 asp, gly, and ser. Reaction ofthe nonapeptide
with
Sanger's
reagent
(1-fluoro-2,4-dinitrobenzene)
followed
byhydrolysis
N-(2,4-dinitrophenyl)alanine. Partial hydrolysis of the nonapeptide gave the following fragments:
gly-ala-phe
ala-asp-gly-ala
phe-ser-ala
ser-ala-phe-asp
Which one of the following is the nonapeptide's primary structure?
1) ala-asp-gly-ala-asp-ala-phe-ser-phe
2) ala-phe-asp-gly-ala-asp-ser-phe-ala
3) ala-asp-gly-ala-phe-ser-ala-phe-asp
4) gly-ala-phe-ser-ala-phe-asp-asp-ala
36
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有机化学双语教学补充材料
王俊儒等编
15 Adjacent polypeptide chains in the β-pleated sheet structure of a protein are held together by:
1) peptide bonds 2) disulfide bridges 3) hydrogen bonds 4) ionic bonds
16 Which one of the following reagents is used for the visual detection of amino acids?
1)Sanger's reagent
2)dicyclohexylcarbodiimide (DCCI)
3)ninhydrin
4)phenyl isothiocyanate
17 Which of the following are used for N-terminal analyses of peptides and proteins?
1)
Sanger's reagent
2)
Edman degradation
3)
dansylation
4)
all of these
18 Which of the following is the mechanism by which Sanger's reagent reacts with N-terminal amino acids?
1)
electrophilic aromatic substitution
2)
nucleophilic aromatic substitution (addition-elimination mechanism)
3)
nucleophilic aromatic substitution (elimination-addition mechanism)
4)
bimolecular nucleophilic substitution (SN2)
19 Which one of the following is the final product of the reaction sequence shown below?
20 Identify the missing starting reagent needed in the Strecker synthesis of isoleucine.(Assume you will get
all the stereoisomers of isoleucine.)
21 Hydrogen bonding or ionic bonding between side chains of a protein or peptide often contributes to the
_________________ of the protein or peptide.
1)
primary structure
2)
secondary structure
3)
tertiary structure
4)
quaternary structure
22 Which of the following analyses for the N-terminal amino acid of a peptide does not require hydrolysis of
the peptide chain?
1)
Edman degradation
2)
Dansylation
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理学院应用化学系有机化学教研室
3)
Sanger’s reagent
4)
None of these require hydrolysis
23 What is the met charge on lysine tat pH of 1.0?
1)+1
24
2)+2
4)+4
3)+3
Sanger’s reagent(1-fluoro-2,4-dinitrobenzene) reacts with the N-terminal amino acids and the side
chains of ______ in peptides and proteins.
1)lysine
2)cysteine
3)glutamic acid
4)phenylalanine
25 Two cyxteine side chains of a polypeptide are often connected to each other by a(an):
1) ionic bond
2)hydrogen bond
3)disulfide bond
4)peptide bond
26 In aqueous solution, the artificial sweetner aspartame slowly converts to the cyclic compound shown
below. Propose a mechanism for this reaction.
27. The imidazole ring of the histidine side chain acts as a proton acceptor in certain enzymecatalyzed
reactions. Which is the more stable protonated form of the histidine residue, A or B? Why?
HN
H
H
N
O
CH2CHC
N
N
H
O
CH2CHC
NH
NH
A
B
EXAM 1
1. (15 points) Write complete names for each of the following, including stereochemistry if it is specifically
shown.
a)
b)
c)
2. (15 points) Arrange each of the following in order with respect to the property indicated. Write “MOST”
under the compound with the highest value and “LEAST” under the compound with the lowest value ( or
“EQUAL” if appropriate).
a) nucleophilicity
H2O / NaOH / NaSH
b) nucleophilicity
NaI / NaBr / I2
c) optical rotation (absolute value)
(R)-2-chloropentane / (S)-2-chloropentane / racemic-2-chloropentane
d) rate of hydrolysis in neutral water
e) rate of reaction with NaN3 in DMSO
38
有机化学双语教学补充材料
王俊儒等编
3. (15 points) Complete each of the following reactions by adding the missing part: either the starting
compound, the necessary reagents and conditions, or the final major product. Show stereochemistry if it is
specific.
a)
b)
c)
d &e)
4a. (10 points) Complete the reaction shown below, initially ignoring stereochemistry.
If the original compound is the (R) stereoisomer, the product is expected to be:
(R) / (S) / racemic / can’t tell / other
If the original compound has an optical rotation that is (+), the product is expected to be:
(+) / (-) / optically inactive / can’t tell / other
4b. (10 points) Complete the reaction shown below, initially ignoring stereochemistry.
If the original compound is the (R) stereoisomer, the product is expected to be:
(R) / (S) / racemic / can’t tell / other
If the original compound has an optical rotation that is (+), the product is expected to be:
(+) / (-) / optically inactive / can’t tell / other
5. (15 points) Examine the pairs of structures below and identify their relationship to one another, using the
letter codes below:
A - the identical structure
D – diastereomers
a)
B - constitutional isomers
E – enantiomers
F - none of the above
b)
c)
d)
C - conformational isomers
e)
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理学院应用化学系有机化学教研室
6a. (12 points) Write a complete mechanism for the solvolysis (substitution only) reaction shown below. Show
all steps and electron pushing arrows. Do not consider any rearrangements.
6b. (8 points) In order to help relieve the ring strain, a cation rearrangement can occur. Write a clear
electron-pushing mechanism that illustrates how a larger ring may be formed and show the final product that
would result.
EXAM 2
Section I - Nomenclature (4 points each,24 points in all)
In the space provided, give the best IUPAC name(both in Chinese and English) for each of the
compounds shown on the right.
H
O
H2
C
H
O
O
H
3
HH
C
H
H
O
O
3.
H
H
O
2.
H
3
H
C
1.
Cl
OH
H
O
H
O
H
O
4.
6.
N
2
O
Section II
5.
CH3C CCHCH CH2
CH2CH3
Multiple Choice (2 points each,30 points in all)
For each of the questions below, circle the letter corresponding to
This bond
the most
correct answer.
7. What orbitals overlap to form the indicated C-C bond?
a) sp3-sp2
c) sp-sp2
b) sp2-sp2
d) sp-sp3
8. Which carboxylic acid is the strongest acid?
Cl
a.
O
OH
OH
O
b.
F
OH
Br
O
c.
OH
O
d.
OH
9. Which of the following is the strongest base?
H
H
a.
N
O
N
N
b.
c.
d.
10. Which of the following species is the most stable cation?
)
d
)
c
)
b
)
a
11. Which of the following molecules meets the Hückle definition for aromaticity:
.
e
.
d
.
c
.
b
.
a
12. An unknown compound gives a copious yellow precipitate（大量黄色沉淀） when it is reacted with
2,4-dinitrophenylhydrazine（2.4－二硝基苯肼） reagent; you can say with certainty that the unknown
40
有机化学双语教学补充材料
王俊儒等编
compound:
a). is a ketone
b). is a ketone or an aldehyde
d). a and c are both correct
c). is a methyl ketone
e). this qualitative test yields ambiguous results; none of the above are
Br
correct
13. What R and/or S configuration notation would be used
a) 2R,3R;
b) 2S, 3R
c) 2R, 3S;
d) 2S, 3S
H
OH
Cl
D
for this structure?
14. Which of the following groups in benzenes are meta-directors toward the aromatic electrophilic
substitution reactions?
1. –COOCH3
a) 1,2 ;
2. -CH2CH3
b) 1,3 ; c) 2,4;
3. -CHO
d) 3,4 ;
4.
-OCH3
e) 4,5
OH
15. Which of the molecules below is a meso
a) I ; b) II ;
c) III ;
5. Br
HO
d) both I and II
OH
HO
II
I
Br
HO
III
stereoisomer?
16. Which of the molecules below is the quickest towards hydrolysis in acidic conditions?
O
O
O
O
a.
OH
O
NH
c.
b.
O
O
d.
O
O
17. Which of the molecules below has the highest amount of enol form at equilibrium?
O
O
O
a.
b.
c.
H
O
O
d.
O
H
H
18. Which of the following would be used for the anti-Markovnikov addition of water to an alkene without
rearrangement?
a) H2O, H2SO4 ;
b) Hg(OAc)2, H2O; then NaBH4;
c) H2SO4; then H2O/heat; d) BH3/THF: then H2O2/NaOH
19. Identify the mechanistic pathways, respectively, used in the formation of the products in the following
reaction.
CH3CH2OH
Br
a) E1, SN1;
b) E2, SN1;
c) E1, SN2;
OCH2CH3
d) E2, SN2
20. Which one of these structures, shown in Fischer projections, represents a chiral molecule?
a) I ;
Section III
b) II;
c) III;
d) IV
Reactions and Synthesis（36 points in all）
Draw the major product for each of the following reactions; you should assume that "excess
reagents" are present, if appropriate. Show product regiochemistry and stereochemistry where
appropriate (2 points each).
C
0
5
0
,
l
C
H
+
2
O
N
a
N
.
1
l
C
H
+
2e
O F
N
）
r
B
u
C
.
2
（
（
21.
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）
理学院应用化学系有机化学教研室
COOH
SOCl2
22.
（
）
CH3NH2
（
）
LiAlH4
（
）
1. K2Cr2O4, H2SO4, H2O
H
OH
2. CH3CH2MgBr, ether
3. H3O+
23.
（
）
(
) +(
O
H3O
N
+
24.
O
O
1.NaOEt/EtOH
25.
)
CH3
EtO
OEt
O
2.CH3CH2I
（
1.NaOEt/EtOH
）
（
2.CH3I
）
O
H
+
H
NaOH
（
H
）
26.
Na2Cr2O7
CH3
27.
H2SO4 H2O
(
)
Heat
Synthesis(4 points each, Note: you need only to choose any three from 30-33)
O
O
O
OC2H5
28.
Cl
Br
29.
COOH
30.
O
31.
Br
O
SECTION IV MECHANISMS(5 points each)
Br2
Hv
Br
32.
33. Write a complete mechanism for the base-catalyzed aldol reaction shown below. Show all steps and all
resonance forms for any intermediates involved.
EXAM 3
42
有机化学双语教学补充材料
王俊儒等编
Section I - Nomenclature (2.5 points each)
In the space provided, give the best IUPAC name(both in Chinese and English) for the compound shown on
the right.
2.______________
1._________________
3.________________
4.______________
5._______________
6.____________
8.________________
7._______________
Section II
Multiple Choice (2 points each)
For each of the questions below, circle the letter corresponding to the most correct answer.
6. Which of the compounds shown below will react with methyl formate (methyl methanoate) in the presence
of methoxide anion(CH3O-) to give a compound, which on treatment with aqueous acid and gentle heating,
will decarboxylate to form butanal?
7. Which of the compounds shown below will react with dimethyl malonate (methyl methyl propanedioate) in
the presence of methoxide anion to give a compound, which on treatment with aqueous acid and gentle
heating, willdecarboxylate and form pentanoic acid?
8. An unknown compound gives a copious yellow precipitate when it is reacted with
2,4-dinitrophenylhydrazinereagent; you can say with certainty that the unknown compound:
a. is a ketone
b. is a ketone or an aldehyde
d. a and c are both correct
c. is a methyl ketone
e. this qualitative test yields ambiguous results; none of the above are correct
9. Reaction of an unknown compound with acidic potassium permanganate (KMnO4) yields a carboxylic acid
and CO2; the unknown compound is:
a. a tetra-substituted alkene
b. a disubstituted alkyne
d. a terminal alkene with one alkyl substituent
c. a tri-substituted alkene
e. a trans, disubstituted alkene
10. In order for a molecule to be aromatic:
a. it must be planar, cyclic and consist of adjacent sp2 atoms containing 4n+2 π-electrons
b. it must have at least two electrons in each of the degenerate molecular orbitals describing the π-system
c. heteroatoms must rehybridize so that all unshared pairs of electrons can contribute to the π-system
d. a and b only are both true
e. a, b and c are all correct
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理学院应用化学系有机化学教研室
11. Which of the following molecules meets the Hückle definition for aromaticity:
12. The absolute configurations of the two chiral centers in the molecule shown below are (given as TOP,
BOTTOM):
a. R, R
c. R, S
b. S, S and the compound is meso
d. S, R
e. S, R and the compound is meso
13. For each of the following molecules indicate in the space immediately under the small letter:
i. if the molecule is chiral, indicate total number of chiral centers
ii. if the molecule contains no chiral centers, indicate "achiral"
iii. if the molecule is a meso compound, do not indicate the number of chiral centers, but indicate "meso"
14. For the molecule shown below, in it's most stable conformation:
a. Two of the methyls are axial.
b. Two of the methyl groups are equatorial.
c. All of the methyl groups are axial.
d. All substituents are equatorial.
e. None of the above are correct
Section III Reactions
15. Draw the major product for each of the following reactions; you should assume that "excess reagents" are
present, if appropriate. (2 points each)
44
有机化学双语教学补充材料
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16. For the aldol condensation shown below, give the structures of the starting material,the reactive enolate
anion (show the attack step using "curved arrows"), and the resulting hydroxyketone (4 points for each box).
17. For the Claisen condensation shown below, give the structures of the starting material, the tetrahedral
addition intermediate, and the resulting condensation product (4 points for each box).
18. Suggest a synthesis of acetophenone, beginning with the following: (4 points each)
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理学院应用化学系有机化学教研室
19. Synthesis problems: (4 points each)
ANSWERS
Section A - Structure And Bonding(1. c 2. a 3. c 4. c 5. c )
Section B - Alkanes And Cycloalkanes(1. d 2. d 3. d 4. c 5. a 6. d 7. a 8. b)
Section D - Stereochemistry(1. d 2. b 3. d 5. c )
Section E - Nucleophiles And Electrophiles(1: 4 2:2 3: 1 4: 4)
Section F - Reactions And Mechanisms(1. B 2. C 3. E 4. A 5. D 6. C )
Section G - Acid-base Reactions(1. b 2. d 3. d 4. d )
Section H - Alkenes And Alkynes
(1. c 2. c 3. d 4. b 5. c 6. b 7. c 8. b 9. b 10. b 11. d 12. d 13. b 14. a 15. c )
Section I - Aromatic Chemistry(1. c 2. d 3. c 4. b 5. c 6. d )
Section J - Aldehydes And Ketones
1: 3 2: 4 3: 3 4: 4 5: 4 6: 3 7: 3 8: 2 9: 2 10: 1 11: 1 12: 1 13: 4 14: 1
15: 2 16: 2 17: 1 18: 4 19: 3 20: 1 21: 3 22: 3 23: 1 24: 1 25: 2
26: 4 27: 2 28: 1 29: 2 30: 1 31: 2 32: 2 33: 4 34: 3 35: 4
Section K - Carboxylic Acids And Carboxylic Acid Derivatives
1: 1 2: 2 3: 2 4: 4 5: 2 6: 3 7: 1 8: 4 9: 1 10: 2 11: 4 12: 2 13: 3
14: 2 15: 4 16: 3 17: 3 18: 3 19: 2 20: 2 21: 1 22: 2 23: 4 24: 1 25: 3 26: 3 27: 3
CARBOXYLIC ACID DERIVATIVES
1: 1 2: 3 3: 1 4: 2 5: 4 6: 1 7: 1 8: 2 9: 2 10: 4 11: 3 12: 1 13: 2 14: 4 15: 2 16: 4
17: 4 18: 1 19: 3 20: 2 21: 1 22: 2 23: 3 24: 1 25: 2 26: 4 27: 4 28: 1
Section L - Halides
PART II
1: 1 2: 1 3: 4 4: 2 5: 3 6: 3 7: 2 8: 1 9: 3 10: 3 11: 3 12: 2 13: 3 14: 1 15: 1 16: 2
17: 1 18: 3 19: 4 20: 1 21: 2 22: 3 23: 1
Section M - Alcohols, Phenols, And Thiols
Alcohols And Thiols
1: 4 2: 4 3: 2 4: 3 5: 4 6: 3 7: 2 8: 2 9: 1 10: 2 11: 4 12: 1 13: 2 14: 3 15: 1 16: 3
17: 2 18: 3 19: 1 20: 1 21: 1 22: 3 23: 2 24: 1 25: 2 26: 4 27: 2 28: 4 29: 1 30: 3
Phenols
1: 4 2: 2 3: 4 4: 2 5: 2 6: 3 7: 4 8: 2 9: 3 10: 4 11: 3 12: 1
13: 3 14: 1 15: 2 16: 1 17: 4 18: 3 19: 3 20: 4 21: 2 22: 4 23: 3
Ethers Epoxides
1: 1 2: 2 3: 2 4: 2 5: 3 6: 3 7: 1 8: 3 9: 2 10: 1 11: 3 12: 2 13: 3 14: 3
15: 1 16: 2 17: 1 18: 1 19: 1 20: 3 21: 1 22: 2 23: 4 24: 1 25: 2 26: 3
27: 4 28: 2 29: 4 30: 2 31: 2 32: 3 33: 1
Section O - Amines And Nitriles
1: 1 2: 3 3: 3 4: 4 5: 4 6: 4 7: 2 8: 1 9: 2 10: 3 11: 2 12: 2 13: 2
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有机化学双语教学补充材料
14: 1 15: 2 16: 2 17: 4 18: 3 19: 3 20: 4 21: 1 22: 2 23: 2 24: 3 25: 1 26: 2
Section P - SPECIAL TOPICS: BIOMOLECULES
P-I Carbohydrates(Saachrides) Key
1: 3 2: 3 3: 4 4: 2 5: 3 6: 2 7: 2 8: 1 9: 4 10: 1 11: 3 12: 2
13: 3 14: 2 15: 1 16: 3 17: 4 18: 1 19: 1 20: 1 21: 2 22: 2 23: 2 24: 3 25: 2
P-II Amino Acids, Peptides, And Proteins key
1: 3 2: 3 3: 3 4: 4 5: 4 6: 4 7: 2 8: 2 9: 2 10: 4 11: 1 12: 1 13: 1
14: 3 15: 3 16: 3 17: 4 18: 2 19: 2 20: 4 21: 3 22: 1 23: 2 24: 1 25: 3
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理学院应用化学系有机化学教研室
Glossary of Organic Chemistry
Acetate(醋酸盐). (CH3COO-, C2H3O2-). acetate ion.
1. an ion formed by removing the acidic hydrogen of acetic acid, HC2H3O2. 2. a compound derived by
replacing the acidic hydrogen in acetic acid. 3. A fiber made of cellulose acetate.
Acetic acid(乙酸). (CH3COOH, C2H4O2). ethanoic acid; vinegar acid; methanecarboxylic acid.
A simple organic acid that gives vinegar its characteristic odor and flavor. Glacial acetic acid is pure
acetic acid.
Acetone ( 丙 酮 ).[CH3COCH3 or (CH3)2CO]. trivial name for propanone, formed by the oxidation of
2-propanolwith KMnO4.
Achiral(非手性的). A molecule that's superimposable on its mir ror image. Achiral molecules do not rotate
plane-polarized light.
Achiral molecule(非手性分子). a molecule that does not contain a stereogenic carbon; an achiral molecule
has a plane ofsymmetry and is superimposable on its mirror image.
Acid anhydride（酸酐）[(RCO)2O]. Compare with acid .
Nonmetallic oxides or organic compounds that react with water to form acids . For example, SO2, CO2,
P2O5, and SO3 are the acid anhydrides of sulfurous, carbonic, phosphoric, and sulfuric acids,
respectively. Acetic anhydride (CH3CO)2O) reacts with water to form acetic acid.
Acid dissociation constant（酸电离常数）.
(Ka) acid ionization constant. Compare with base hydrolysis constant.
The equilibrium constant for the dissociation of an acid into a hydrogen ion and an anion. For
example, the acid dissociation constant for acetic acid is the equilibrium constant for HC2H3O2(aq)
H+(aq) + C2H3O2-(aq), which is Ka = [H+][C2H3O2-]/[HC2H3O2].
Acid halide(酰卤)（RCOX）. acid chloride; acyl halide; acyl chloride.
Compounds containing a carbonyl group bound to a halogen atom.
Acid(酸). (Lat. acidus, sour) Compare with base.
A proton donor or an electron pair acceptor. 1. a compound which releases hydrogen ions (H+) in
solution (Arrhenius). 2. a compound containing detachable hydrogen ions (Bronsted-Lowry). 3. a
compound that can accept a pair of electrons from a base (Lewis)..
Acid-base indicator(酸碱指示剂).
A weak acid that has acid and base forms with sharply different colors. Changes in pH around the
acid's pKa are "indicated" by color changes.
Acid/base reaction（酸/碱反应）. a reaction in which an acidic H atom is transferred from one molecule to
another.
Addition compound(加成化合物). complex compound. Compare with hydrate.
An addition compound contains two or more simpler compounds that can be packed in a definite ratio
into a crystal. A dot is used to separate the compounds in the formula. For example, ZnSO4·7 H2O is
an addition compound of zinc sulfate and water. This represents a compound, and not a mixture,
because there is a definite 1:7 ratio of zinc sulfate to water in the compound. Hydrates are a common
type of addition compound.
Addition reaction(加成反应). A reaction in which two molecules are combined to yield a
single product. Typical of the reactions of alkenes and alkynes.
-al(醛，后缀). A suffix added to the systematic names of organic compounds that contain an aldehyde group
-(C=O)-H. For example, the systematic name of acetaldehyde, CH3CHO, is ethanal.
Alcohol(醇). (ROH) Compare with phenol and hydroxide.
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A molecule containing a hydroxyl (OH) group. Also a functional group. An alcohol is an organic
compound with a carbon bound to a hydroxyl group. Examples are methanol, CH3OH; ethanol,
CH3CH2OH; propanol, CH3CH2CH2OH. Compounds with -OH attached to an aromatic ring are called
phenols rather than alcohols.
Aldehyde(醛). (RCHO)
A molecule containing a terminal carbonyl (CHO) group. Also a functional group. An aldehyde is an
organic compound with a carbon bound to a -(C=O)-H group. Examples are formaldehyde (HCHO),
acetaldehyde, CH3CHO, and benzaldehyde, C6H6CHO.
Aliphatic(脂肪族的). Compare with aromatic .
An organic compound that does not contain ring structures.
Alkaline earth(碱土金属). An oxide of an alkaline earth metal, which produces an alkaline solution in reaction
with water.
Alkali metal(碱金属). (a metal in Group IA on the periodic table): active metals which may be used to react
with analcohol to produce the corresponding metal alkoxide and hydrogen gas.
Alkaline(碱的，碱性的). Having a pH greater than 7.
Alkane(烷烃). (RH，CnH2n+2)
paraffin. Compare with hydrocarbon and alkene. A molecule containing only
C-H and C-C single bonds. A series of organic compounds with general formula CnH2n+2. Alkane names end
with -ane. Examples are propane (with n=3) and octane (with n=8).
Alkene(烯烃). (CnH2n) A molecule containing one or more carbon-carbon double bonds. Also a functional
group. A compound that consists of only carbon and hydrogen, that contains at least one carbon-carbon
double bond. Alkene names end with -ene. Examples are ethylene (CH2=CH2); 1-propene (CH2=CH2CH3),
and 2-octane (CH3CH=CH(CH2)4CH3).
Alkoxide(醇盐, 烷氧根负离子). (RO- M+) alkoxide ion.
An ionic compound formed by removal of hydrogen ions from the hydroxyl group in an alcohol using
reactive metals, e.g. sodium. For example, potassium metal reacts with methanol (CH3OH) to
produce potassium methoxide (KOCH3).
Alkoxy group（烷氧基）(RO-).a substituent containing an alkyl group linked to an oxygen.
Alkyl benzene（烷基苯）(C6H5-R). a benzene ring that has one alkyl group attached; the alkyl group
(exceptquaternary alkyl groups) is susceptible to oxidation with hot KMnO4 to yield benzoic acid
(C6H5CO2H).
Alkyl(烷基). (-CnH2n+1) alkyl group. A molecular fragment derived from an alkane by dropping a hydrogen
atom from the formula. Examples are methyl (-CH3) and ethyl (-CH2CH3).
Alkyne(炔烃). (CnH2n-2) A molecule containing one or more carbon-carbon triple bonds. Also a functional
group. A compound that consists of only carbon and hydrogen, that contains at least one carbon-carbon
triple bond. Alkyne names end with -yne. Examples are acetylene (CH CH); 1-propyne (CH CCH3), and
2-octyne (CH3C C(CH2)4CH3).
Allenes(丙二烯). Propa-1,2-diene (CH2=C=CH2) and derivatives. In allenes the two πbonds are orthogonal
(see below), as are the two terminal hydrogens at one end, with respect to those at the other.
Allo-(同分异构的).
prefix that designates the more stable of a pair of geometric isomers. allo- is sometimes
used less precisely to designate isomers or close relatives of a compound.
Allyl(烯丙基). allylic; allyl group; allyl radical.
A molecular fragment derived by removing a methyl hydrogen from propene (-CH2-CH=CH2). For
example, "allyl chloride" is 3-chloropropene, Cl-CH2-CH=CH2.
Allylic carbon(烯丙基正离子). (CH2=CH-CH2+)
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An sp3 carbon adjacent to a double bond.
Amide(酰胺)(RCONH2). A molecule containing a carbonyl group attached to a nitrogen (-CONR2). Also a
functional group. An amide is an organic compound that contains a carbonyl group bound to nitrogen:
.
The simplest amides are formamide (HCONH2) and acetamide (CH3CONH2).
Amine(胺)(RNH2). Compare with ammine.
A molecule containing an isolated nitrogen = (NR3). Also a functional group. An amine is an organic
compound that contains a nitrogen atom bound only to carbon and possibly hydrogen atoms.
Examples are methylamine, CH3NH2; dimethylamine, CH3NHCH3; and trimethylamine, (CH3)3N.
Amino acid(氨基酸). Amino acids are molecules that contain at least one amine group (-NH2) and at least
one carboxylic acid group (-COOH). When these groups are both attached to the same carbon, the acid is an
-amino acid.
-amino acids are the basic building blocks of proteins.
Amino group（氨基）. the -NH2 group.
Ammine(氨络物). Compare with amine.
A metal ion complex containing ammonia as a ligand. The ammonia nitrogen is bound directly to a
metal ion in ammines; amines differ in that the ammonia nitrogen is directly bound to a carbon atom.
Ammonia(氨，氨水). (NH3) Compare with ammonium.
Pure NH3 is a colorless gas with a sharp, characteristic odor. It is easily liquified by pressure, and is
very soluble in water. Ammonia acts as a weak base. Aqueous solutions of ammonia are (incorrectly)
referred to as "ammonium hydroxide".
Ammonium ion(铵根离子). (NH4+) ammonium.
NH4+ is a cation formed by neutralization of ammonia, which acts as a weak base.
Amphiprotic solvent(两性溶剂). Compare with aprotic solvent.
Solvents that exhibit both acidic and basic properties; amphiprotic solvents undergo autoprotolysis.
Examples are water, ammonia, and ethanol.
Amphoteric(两性的). ampholyte.
A substance that can act as either an acid or a base in a reaction. For example, aluminum hydroxide
can neutralize mineral acids ( Al(OH)3 + 3 HCl = AlCl3 + 3 H2O ) or strong bases ( Al(OH)3 + 3 NaOH =
Na3AlO3 + 3 H2O).
Aniline（苯胺；苯胺的）. (C6H5NH2).a primary (1　) amine in which the NH2 group is bonded directly to a
benzene ring.
Ångstrom (Å)(埃，1/10 纳米).
Unit of length named after the Swedish physicist, now being superseded by nanometer (nm). 1 Å =
10–10 m so that a bond length of 1.54 Å is given by 0.154 nm.
Anhydrous(无水的). anhydrous compound; anhydride. Compare with hydrate.
A compound with all water removed, especially water of hydration. For example, strongly heating
copper(II) sulfate pentahydrate (CuSO4·5H2O) produces anhydrous copper(II) sulfate (CuSO4).
Anion(阴离子). Compare with cation.
A negatively charged atom or molecule. An anion is a negatively charged ion. Nonmetals typically
form anions.
Anomers(异头物). Anomers are cyclic diastereoisomers that differ only at the hemiacetal carbon. The
anomeric carbon in a sugar is the only carbon that is bonded to two oxygen atoms.
Anti(希腊字头，反；抗；对；阻) (see also Anti addition; Anti periplanar). Substituents are anti if they are on
opposite sides of a defined reference plane in a molecule. Anti is used to assign stereochemistry to
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products of, for example, asymmetric aldol reactions. The main chain is drawn in the plane of the
paper and substituents on opposite sides of the plane are termed anti.
Anti addition(反式加成). A reaction in which the two groups of a reagent X-Y add on opposite faces of a
carbon-carbon bond. Anti addition of X–Y occurs when X and Y are added to opposite faces of a
double bond.
Anti clinal(反错构象). When the C–C–C–C dihedral angle is between 90° and 150°, i.e. 120 30°, the
conformation is said to be anti clinal.
Anti conformation(反式构象). A type of staggered conformation in which the two big groups are opposite of
each other in a Newman projection.
Anti periplanar (sometimes called Anti)( 反 式 共 平 面 ). Term given to a molecular fragment, e.g.
X–C(1)–C(2)–Y, or C(1)–C(2)–Y (in this second case, a lone pair of electrons in a p-orbital replaces
the X–C bond), in which the dihedral angle is 180°, or more generally 180 30°.
Anti-aromatic(反芳香性的). A highly unstable planar ring system with 4n pi electrons.
Antibonding orbital(反键轨道). antibonding; antibonding molecular orbital.
A molecular orbital that can be described as the result of destructive interference of atomic orbitals
on bonded atoms. Antibonding orbitals have energies higher than the energies its constituent atomic
orbitals would have if the atoms were separate.
Anti-periplanar (a.k.a. anticoplanar)(反平面). The conformation in which a hydrogen and a leaving group
are in the same plane and on opposite sides of a carbon-carbon single bond. The conformation
required for E2 elimination.
Aprotic solvent(非质子溶剂；疏质子溶剂). Compare with amphiprotic solvent.
Solvents that do not contain O-H or N-H bonds. A solvent that does not act as an acid or as a base;
aprotic solvents don't undergo autoprotolysis. Examples are pentane, pet ether, and toluene.
Aqua regia(王水).
A mixture of nitric and hydrochloric acids, usually 1:3 or 1:4 parts HNO3 to HCl, used to dissolve gold.
Arene(芳香烃). (ArH)
A hydrocarbon that contains at least one aromatic ring.
Aromatic(芳香族的). A planar ring system that contains uninterrupted p orbitals around the ring and a total of
4n+2 pi electrons. Aromatic compounds are unusually stable compounds.
Aromatic compound(芳族化合物).
A compound containing an aromatic ring. Aromatic compounds have strong, characteristic odors.
Aromatic ring(芳环). (Ar)
An exceptionally stable planar ring of atoms with resonance structures that consist of alternating
double and single bonds, e. g. benzene:
Aryl(芳基). (Ar-) aryl group.
An aromatic group as a substituent. A molecular fragment or group attached to a molecule by an
atom that is on an aromatic ring.
Aspirin（阿司匹林；乙酰水杨酸）.trivial name for the compound acetylsalicylic acid; formed by treating salicylic
acid with aceticanhydride.
Asymmetric carbon atom（不对称碳原子；手性碳原子）. a carbon atom with four different substituents; a
stereogenic carbon.
Atactic(不规则的). This adjective describes a polymer whose stereogenic centres along the polymer chain
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are randomly oriented.
Atropisomers(位阻异构体). Stereoisomers that arise from restricted rotation around a single bond in which
the barrier to rotation is sufficiently high for the stereoisomers to be isolated. Certain ortho
disubstituted biphenyls are atropisomers, and the stereoisomers referred to in this case are
enantiomers.
Average bond enthalpy(平均键焓). Compare with bond enthalpy.
Average enthalpy change per mole when the same type of bond is broken in the gas phase for many
similar substances
Axial bonds(直立键). A bond perpendicular to the equator of the ring (up or down), typically in a chair
cyclohexane. In the chair conformation of cyclohexanes, axial bonds are described as being: (a)
parallel to the C3 axis, or (b) perpendicular to a general plane that contains the majority of carbon
atoms.
Axial chirality(轴手性；轴不对称 ). Chirality that has its origins in the non-planar disposition of groups with
respect to an axis,and exemplified by 1,3-dichloroallene, certain alkylidenecyclohexanes and
4-substituted cyclohexanone oximes.
Axial(轴的).
1. An atom, bond, or lone pair that is perpendicular to equatorial atoms, bonds, and lone pairs in a
trigonal bipyramidal molecular geometry.
Azo(偶氮). azo compound; azo group; azo dye.
The azo group has the general structure Ar-N=N-Ar', where Ar and Ar' indicate substituted aromatic
rings. Compounds containing the azo compounds are often intensely colored and are economically
important as dyes. Methyl orange is an example of an azo dye.
Base hydrolysis constant(碱水解常数). (Kb) base ionization constant; basic hydrolysis constant. Compare
with acid dissociation constant.
The equilibrium constant for the hydrolysis reaction associated with a base. For example, Kb for
ammonia is the equilibrium constant for NH3(aq) + H2O( )
NH4+(aq) + OH-(aq), or Kb =
[NH4+][OH-]/[NH3].
Base(碱). alkali; alkaline; basic. Compare with acid.
A proton acceptor or an electron pair donor.
1. a compound that reacts with an acid to form a salt. 2. a compound that produces hydroxide ions in
aqueous solution (Arrhenius). 3. a molecule or ion that captures hydrogen ions.(Bronsted-Lowry). 4. a
molecule or ion that donates an electron pair to form a chemical bond.(Lewis).
Benzaldehyde（苯甲醛；安息香醛）.(C6H5CHO).simplest aromatic aldehyde, formed by the controlled
oxidation of benzyl alcohol; vigorous oxidation yields benzoic acid.
Benzene（苯）. an aromatic cyclic hydrocarbon of formula C6H6.
Benzoic acid（苯甲酸）(C6H5CO2H): simplest aromatic carboxylic acid, formed by the vigorous oxidation of
alkyl benzene, benzyl alcohol, and benzaldehyde.
Benzyl group(苄基；苯甲基) (C6H5CH2-). A benzene ring plus a methylene (CH2) unit (C6H5-CH2-).
Benzylic position( ). The position of a carbon attached to a benzene ring.
Benzyne(苯炔; 脱氢苯). A highly reactive intermediate. A benzene ring with a triple bond.
Bicyclic(二环的). A molecule with two rings that share at least two carbons.
Binary compound(二元化合物). Compare with compound.
A compound that contains two different elements. NaCl is a binary compound; NaClO is not.
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Bond energy(键能). bond enthalpy(键焓).Compare with bond enthalpy.
Energy change per mole when a bond is broken in the gas phase for a particular substance.
Bond length(键长).
The average distance between the nuclei of two bonded atoms in a stable molecule.
Bond order(键级).
1. In Lewis structures, the number of electron pairs shared by two atoms. 2. In molecular orbital theory,
the net number of electron pairs in bonding orbitals (calculated as half the difference between the
number of electrons in bonding orbitals and the number of electrons in antibonding orbitals.
Bridgehead carbon(桥头碳原子). In an unsubstituted hydrocarbon that consists of two or more fused or
bridged rings, with two or more carbons in common, the bridgehead carbons are tertiary carbons
common to two or more rings. Bridgehead carbons can be substituted by, for example, Cl,OH, etc. In
bicyclo[2.2.1]heptane the bridgehead carbons are C(1) and C(4); in bicyclo[4.4.0]decane they are
C(1) and C(6).
Brösted acid(布朗斯特酸). Compare with acid.
A material that gives up hydrogen ions in a chemical reaction.
Brösted base(布朗斯特碱). Compare with base.
A material that accepts hydrogen ions in a chemical reaction.
Brosylate (4-bromobenzenesulfonate, 4-BrC6H4SO3)(对甲基苯磺酸盐). Slightly mbetter leaving group
group than tosylate in substitution and elimination reactions. Usually abbreviated to OBs.
Buffer(缓冲液). pH buffer; buffer solution.
A solution that can maintain its pH value with little change when acids or bases are added to it.
Buffer solutions are usually prepared as mixtures of a weak acid with its own salt or mixtures of salts
of weak acids. For example, a 50:50 mixture of 1 M acetic acid and 1 M sodium acetate buffers pH
around 4.7.
Cahn–Ingold–Prelog (CIP) R/S convention(R/S构型命名法 ). The most widely used method for assignment
of configuration to stereogenic centres (and chiral axes). Substituents at stereogenic centres are
given ranking numbers 1, 2, 3 and 4, associated with decreasing atomic number; configuration is
then assigned as in Chapter 2.
Canonical forms (also called resonance structures)(共振结构式). These are different mLewis structures that
are alternative ways of representing the actual structure of a molecule that contains delocalized
bonds. One draws several possible structures that all have the same number of unpaired electrons,
and in which the relative positions of the nuclei are the same. Each canonical structure contributes in
proportion to its stability, so that the structure is a weighted average of all canonical structures.
These delocalized canonical structures have no individual existence. As an example, aromatic
compounds and amides are weighted averages of two or more canonical forms (or Lewis structures);
in the case of an amide, these are, for example, R12N–C(=O)R2 and R12N+=C(O–)R2.
Carbanion(负碳离子). A negatively charged carbon atom.
Carbene(碳烯). A reactive intermediate, characterized by a neutral, electron-deficient carbon center with two
substituents (R2C:).
Carbocation(碳正离子). A positively charged carbon.
Carbonyl(羰基). carbonyl group.
A carbon double bonded to oxygen (C=O). A divalent group consisting of a carbon atom with a
double-bond to oxygen. For example, acetone (CH3-(C=O)-CH3) is a carbonyl group linking two
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methyl groups. Also refers to a compound of a metal with carbon monoxide, such as iron carbonyl,
Fe(CO)5.
Carboxylic acid(羧酸)(RCOOH). carboxyl; carboxyl group.
A molecule containing a carboxyl (COOH) group.Also a functional group. A carboxylic acid is an
organic molecule with a -(C=O)-OH group. The group is also written as -COOH and is called a
carboxyl group. The hydrogen on the -COOH group ionizes in water; carboxylic acids are weak acids.
The simplest carboxylic acids are formic acid (H-COOH) and acetic acid (CH3-COOH).
Carotene(胡萝卜素).
Carotene is an unsaturated hydrocarbon pigment found in many plants. Carotene is the basic building
block of vitamin A.
Catalyst（催化剂）a substance which changes the rate of a chemical reaction but is unchanged at the end of
the reaction; an example would be the Pt used in the hydrogenation of alkenes.
Cation(阳离子). Compare with anion.
A positively charged molecule or atom. A cation is a positively charged ion. Metals typically form
cations.
Chair conformation(椅式构象). Typically, the most stable cyclohexane conformation. Looks like a chair. The
lowest energy conformation of cyclohexane. All the vicinal C–H bonds are staggered; this
conformation has very little angle strain or torsion strain.
Chelate(螯合的).
A stable complex of a metal with one or more polydentate ligands. For example, calcium complexes
with EDTA to form a chelate.
Chemical bond(化学键). bond; bonding; chemical bonding.
A chemical bond is a strong attraction between two or more atoms. Bonds hold atoms in molecules
and crystals together. There are many types of chemical bonds, but all involve electrons which are
either shared or transferred between the bonded atoms.
Chemical shift(化学位移). The location of an NMR peak relative to the standard tetramethylsilane (TMS),
given in units of parts per million (ppm).
Chiral center(手性中心). asymmetric center.
A carbon or other atom with four nonidentical substituents. An atom in a molecule that causes chirality,
usually an atom that is bound to four different groups. A molecule can have chirality without having a
chiral center, and a molecule may also have more than one chiral centers.
Chiral molecule(手性分子). A molecule that's not superimposable on its mirror image. Chiral molecules rotate
plane-polarized light.
Chiral(手性的). chirality(手性).
Having nonsuperimposable mirror images. For example, a shoe or a glove is chiral.
A chiral (or handed) molecule is one that is not superimposable on its mirror image. The adjective is
ideally restricted to single molecules. An object such as a helix can also be described as chiral.
The property of non-identity of an object with its mirror image. An object, e.g. a molecule in a given
configuration or conformation, is said to be chiral when it is not identical with its mirror image.
Cis(顺式). Groups or atoms are cis when they lie on the same side of an identifiable reference plane in a
molecule.
Two identical substituents on the same side of a double bond or ring.
Concerted(一致的；协同的). In a concerted reaction the bonding changes occur in a single step and
simultaneously.
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Condensation reaction(缩合反应). A reaction in which a small molecule (usually H2O or HX) is produced in
the combination of two other molecules.
Configuration(构型). The three-dimensional arrangement (or sequence) in space of atoms, or functional
groups, that characterizes a stereoisomer. In order to change a configuration, bond breaking and
bond
re-forming
in
a
different
sequence
must
occur.
Enantiomers
have
opposite
configurations.Configurations are denoted by R/S; D/L; E/Z. Configuration should be contrasted with
conformation, in which changes are brought about only by bond rotation.
Conformation (boat)( 船式构象). A conformation of cyclohexane that, by virtue of two eclipsed C–C bonds
and a 1,4 non-bonded H...H interaction, is of higher energy than the chair conformation. So called
because it resembles a boat when viewed sideways on.
Conformation (chair)( 椅式构象). The lowest energy conformation of cyclohexane, in which all C–C bonds
are staggered, and which has very little angle or torsional strain. This conformation resembles a
chair when viewed sideways on.
Conformation (eclipsed)(重叠式构象). When, for example, in ethane the dihedral angle between a pair of
hydrogens on adjacent carbons is 0°; this is the least stable conformation. In butane, both C–C–C–C
dihedral angles of 0　(synperiplanar) and 120　(anticlinal) are eclipsed; the C–H bonds are eclipsed
here also. Some rigid molecules, e.g. bicyclo[2.2.1]heptane, have the C–H bonds at C(2), C(3), C(5)
and C(6) locked in an eclipsed conformation.
Conformation (skewed)(扭曲式构象). As above, but with the value of between 0° and 60°; there are an
infinite number of skewed conformations.
Conformation (staggered)(交叉式构象). As above but with ø= 60°; in the case of ethane, the most stable
conformation. Butane has a gauche staggered conformation in which the C–C–C–C dihedral angle is
60° and an antiperiplanar staggered conformation in which the corresponding dihedral angle is 180°.
Conformation(构象). The instantaneous spatial arrangements of atoms. Conformations can change by
rotation around single bonds. The instantaneous spatial arrangements of atoms. Conformations can change
by rotation around single bonds.
Conformers(构象异构体). conformation(构象).
Molecular arrangements that differ only by rotations around single bonds. For example, the "boat" and
"chair" forms of cyclohexane are conformers.
Conjugate acid(共轭酸). The acid that results from protonation of a base.
Conjugate base(共轭碱). The base that results from the deprotonation of an acid.
Conjugated double bonds( 共 轭 双 键 ). Double bonds separated by one carbon-carbon single bond.
Alternating double bonds.
Conjugation(共轭).A general feature of molecules which haveadjacent p-orbitals as in molecules with
alternating multiple bonds. Electrons are said to be delocalized through extended π bonding.
Conrotatory(顺旋). This adjective indicates that both p-orbitals at the terminal carbons (and the substituents
at these carbons) of a conjugated acyclic hydrocarbon rotate in the same sense, both clockwise or
both anti-clockwise, during ring closure. Also applied to the reverse step, namely ring opening.
Constitutional isomers(构造异构体). Molecules with the same molecular formula but with atoms attached in
different ways.
Coordination number(配位数).
The number of bonds formed by the central atom in a metal-ligand complex.
Coupling constant( 耦合常数). The distance between two neighboring lines in an NMR peak (given in units
of Hz).
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Coupling protons(耦合质子). Protons that interact with each other and split the NMR peak into a certain
number of lines following the n+1 rule.
Covalent bond(共价键 ). covalent; covalently bound. Compare with covalent compound and ionic bond.
Bond in which the two electrons are shared between the two atoms.
A covalent bond is a very strong attraction between two or more atoms that are sharing their electrons.
In structural formulas, covalent bonds are represented by a line drawn between the symbols of the
bonded atoms.
A compound made of molecules- not ions. The atoms in the compound are bound together by shared
electrons. Also called a molecular compound.
Cyclic compound（环状化合物）a molecule which has the two ends of the carbon chain connected together
to form a ring.
Crystal field splitting energy(晶体场分裂能). ( )
Ligands complexed to a metal ion will raise the energy of some of its d orbitals and lower the
energy of others. The difference in energy is called the crystal field splitting energy.
Crystal field theory( 晶体场理论). crystal field.
The color, spectra, and magnetic properties of metal-ligand complexes can be explained by modeling
the effect of ligands on metal's d orbital energies.
Cupric. (Cu2+) cupric ion(二价铜的).
Deprecated. 1. the copper(II) ion, Cu2+. 2. A compound that contains copper in the +2 oxidation state.
Cuprous. (Cu+) cuprous ion(亚铜的 ).
Deprecated. 1. the copper(I) ion, Cu+. 2. A compound that contains copper in the +1 oxidation state.
Cycloaddition reaction( 环化加成反应). In the context of pericyclic reactions, this term refers to two
molecules, the same or different, with one or more bonds, that combine to form a cyclic compound with
creation of two new bonds in a concerted, bimolecular reaction. Of course, cycloaddition reactions may
proceed stepwise, but these are not pericyclic reactions.
D-. D-isomer(D-异构体). Compare with L- .
Prefix used to designate a dextrorotatory enantiomer .
D-. D-isomer(D-异构体). Compare with L-.
Prefix used to designate a dextrorotatory enantiomer.
Dehydration（脱水）an elimination reaction in which an alcohol reacts with concentrated acid to yield an
alkene plus water.
Dehydrogenases(脱氢酶). Enzymes that operate in conjunction with a cofactor,usually NADH. Despite the
name, dehydrogenases catalyse both dehydrogenation (oxidation) and reduction reactions, under
appropriate conditions.
dehydrohalogenation(脱去卤化氢 ). Loss of a hydrohalic acid (like HBr, HCl, and so on) to form a
double bond.
Delta value (a.k.a. d value)(δ：化学位移值). The chemical shift. The location of an NMR peak relative to the
standard tetramethylsilane (TMS), given in units of parts per million (ppm).
Dextrorotatory (d)( 右旋的). Having the property of rotating plane-polarized light clockwise.
Description given to a chiral compound that rotates the plane of polarized light (usually of wavelength
589.6 nm, the sodium D line) in a clockwise sense as the observer looks into the propagating beam.
Diastereoisomers(非对映异构体). Stereoisomers that are not mirror images of each other. Stereoisomers
that are not enantiomers. This is a wide definition, which includes geometric isomers such as, for
example, (Z)- and (E)-1,2-dichloroethene. Note that diastereoisomers may be (a) both chiral, (b) one
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may be chiral and the other not, e.g. tartaric acids (Chapter 3) and (c) both may be achiral, e.g. cisand trans-1,3-disubstituted cyclobutanes and cis-1,4- and trans-1,4-disubstituted cyclohexanes.
Diastereotopic(非对映异构的). This adjective applies to molecules that contain (a) sp3 hybridized carbon,
e.g. C(1), in a molecule of type RC(1)H2–C(2)XYZ (X≠Y≠Z) that contains a stereogenic centre,
usually, but not necessarily, adjacent to C(1). Replacement, separately, of each of the C(1)
hydrogens by D gives two diastereoisomers, and the hydrogens are said to be diastereotopic. (b) An
sp2 hybridized carbon, such as a carbonyl group in a molecule that contains a stereogenic centre,
e.g. MeCOCH(Me)Ph. Attack at the two faces of the carbonyl group by a Grignard reagent RMgBr,
where R ≠Me, gives a pair of diastereoisomeric alcohols, usually in unequal amounts. The faces of
the carbonyl group are said to be diastereotopic.
Diatomic molecule(双原子分子). Compare with binary compound and polyatomic molecule.
A molecule that contains only two atoms. All of the noninert gases occur as diatomic molecules; e. g.
hydrogen, oxygen, nitrogen, fluorine, and chlorine are H2, O2, N2, F2, and Cl2, respectively.
Diazonium salt(重氮盐).
A diazonium salt is a compound with general form Ar-NN+X-, where Ar represents a substituted
benzene ring and X- is a halide ion such as chloride. Diazonium salts are unstable and explosive in
dry form. They are used to manufacture many different organic compounds, including azo dyes. See
also diazotization.
Diazotization(重氮化).
Diazotization is a reaction that converts an -NH2 group connected to a phenyl ring to a diazonium salt.
For example,
Diazotization reactions are extremely useful in organic synthesis. The nitrous acid provides NO+
which replaces a hydrogen on the -NH3+ group to produce -NH2NO+ and water; a second water is
eliminated to produce the -N2+ group.
Dichloromethane(二氯甲烷). (CH2Cl2)
Dichloromethane (CH2Cl2) is an organic solvent often use to extract organic substances from
samples. It is toxic but much less so than chloroform or carbon tetrachloride, which were previously
used for this purpose.
Diels-Alder reaction(狄尔斯-阿尔德反应). A reaction that brings together a diene and a dienophile to form
bicyclic molecules and rings.
Diene(二烯烃). A molecule that contains two alternating double bonds. A reactant in the Diels-Alder reaction.
Dienophile(亲双烯体). A reactant in the Diels-Alder reaction that contains a double bond. Dienophiles are
often substituted with electron-withdrawing groups.
Diol（二醇）a compound with two alcohol groups.
Double bond（双键）a group in which two pairs of electrons are shared between two atoms (C=C,C=O, C=N);
adouble bond is made up of a sigma bond and a pi bon
Dipole moment(偶极矩). A measure of the separation of charge in a bond or molecule.
Disrotatory (see Conrotatory)( 对旋). The opposite of conrotatory; in disrotatoryring closures of conjugated
acyclic hydrocarbons, the p-orbitals at the terminal carbons, together with the substituents at these
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理学院应用化学系有机化学教研室
carbons, rotate in opposite senses, one clockwise and the other anti-clockwise.
DL convention(DL 规 则 ). Employed, frequently in conjunction with Fischer projections, to assign
configuration to sugars and amino acids, with D-glyceraldehyde as reference compound.
Doublet(双重的). Describes an NMR signal split into two peaks.
E isomer(E异构体). Stereoisomer in which the two highest priority groups are on opposite sides= of a ring or
double bond.
Eclipsed conformation(重叠式构象). Conformation about a carbon-carbon single bond in which all of the
bonds off of two adjacent carbons are aligned with each other (0o apart
when
viewed in a Newman projection).
EDTA(乙二胺四乙酸). ethylenediaminetetracetic acid; versine.
A polydentate ligand that tightly complexes certain metal ions. EDTA is
used as
a blood preservative by complexing free calcium ion (which promotes blood
clotting).
EDTA's ability to bind to lead ions makes it useful as an antidote for lead
poisoning.
Efflorescent(风化的). efflorescence; efflorescing. Compare with deliquescent
and hygroscopic.
Efflorescent substances lose water of crystallization to the air. The loss of water changes the crystal
structure, often producing a powdery crust.
Electric dipole moment(电偶极矩). (µ) dipole moment.
A measure of the degree of polarity of a polar molecule. Dipole moment is a vector with magnitude
equal to charge separation times the distance between the centers of positive and negative charges.
Chemists point the vector from the positive to the negative pole; physicists point it the opposite way.
Dipole moments are often expressed in units called Debyes.
Electric dipole(电偶极子). Dipole.
An object whose centers of positive and negative charge do not coincide. For example, a hydrogen
chloride (HCl) molecule is an electric dipole because bonding electrons are on average closer to the
chlorine atom than the hydrogen, producing a partial positive charge on the H end and a partial
negative charge on the Cl end.
Electrocyclic reactions( 电 环 化 反 应 ； π- 键 环 化 反 应 ). A sub-class of pericylic reactions. Concerted
intramolecular ring-forming reactions, e.g. of conjugated dienes or trienes in which a new bond is
formed by way of a cyclic transition state. The cyclic product contains one fewer double bond. Term
also applies to the reverse reaction. The simplest example is interconversion of buta-1,3-diene and
cyclobutene.
Electronegativity(电负性；阴电性). Compare with ionization energy and electron affinity.
A term describing the electron piggishness of an atom. More technically, a measure of the tendency of
an atom to attract the electrons in a covalent bond to itself.
Electronegativity is a measure of the attraction an atom has for bonding electrons. Bonds between
atoms with different electronegativities are polar, with the bonding electrons spending more time on
average around the atom with higher electronegativity.
Electrophile (from Greek ‘electron loving’)( 亲电子试剂). Electron lover. A molecule that can accept a lone
pair of electrons (a Lewis acid).
Term defined by Ingold (J. Chem. Soc., 1933, 1191), together with nucleophile (see below). A reagent
that acquires a share in the electrons of another (foreign) molecule during a reaction. Exemplified by
Br2 in electrophilic bromination of an alkene, and nitronium ion (NO2+) in electrophilic nitration of
benzene. In these reactions the alkene and benzene, respectively, are complementary nucleophiles.
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Element Compare with compound and mixture(元素；成分).
An element is a substance composed of atoms with identical atomic number. The older definition of
element (an element is a pure substance that can't be decomposed chemically) was made obsolete
by the discovery of isotopes.
Elimination reaction(消除反应).A reaction in which a small molecule (typically H2O or HX) is expelled from a
single molecule to form an alkene or alkyne. The two common mechanisms of elimination are known
as the E1 and the E2 reaction.
E1 elimination reaction(单分子消除反应). A reaction that eliminates a hydrohalic acid (like HCl, HBr, etc) to
form an alkene. A first order reaction that goes through a carbocation mechanism.
E2 elimination reaction(双分子消除反应). A reaction that eliminates a hydrohalic acid (like HCl, HBr, etc) to
form an alkene. A second order reaction that occurs in single step, in which the double bond is
formed as the hydrohalic acid is eliminated.
Elution( 洗 脱 ； 洗 剂 ). In column chromatography, which is used to separate compounds (including
enantiomers), a solution of a substrate is poured onto a column of a packing (or stationary phase)
which may be chiral, as in the case of cellulose. The solvent passes downward through the column
and emerges through a tap at the bottom. In so doing there are two opposing factors at work: (a)
adsorption of the substrate(s) on the stationary phase, (b) de-adsorption, or ‘washing-off’ of the
substrate by the solvent. This process of adsorption/de-adsorption is repeated continually as the
substrate moves down the column. The role of the solvent is elution, and a substrate is eluted more
rapidly the less it is adsorbed on the stationary phase. By means of differential diastereomeric
interactions with a chiral stationary phase, it is possible to separate enantiomers.
Empirical formula(经验式；实验式). simplest formula. Compare with molecular formula.
Empirical formulas show which elements are present in a compound, with their mole ratios indicated
as subscripts. For example, the empirical formula of glucose is CH2O, which means that for every
mole of carbon in the compound, there are 2 moles of hydrogen and one mole of oxygen.
Enantiomeric excess; enantiomeric ratio(对映体过量百分数，e.e值). Ways of expressing the enantiomeric
make-up of a sample. A sample that consists of, say, 90% (+) enantiomer and 10% (–) enantiomer
has an enantiomeric excess (ee) of 80% and an enantiomeric ratio of 9:1.
Enantiomerically enriched(enantioenriched ， 对 映 体 过 量 的 ). See scalemic. A sample of a chiral
substance whose enantiomeric ratio is greater than 50:50 but less than 100:0.
Enantiomerically pure (optically pure)( 光学纯). A sample that consists of only one enantiomer.
Enantiomers(对映体). Molecules that are nonsuperimposable mirror ima= ges of each other. A pair of
molecules related as non-superimposable mirror images. They rotate the plane of polarized light in
opposite directions, and for solutions of equal concentration, by equal amounts. Otherwise their
physical properties are identical.
Enantiotopic(对映异位的). Adjective used to describe (a) certain sp3 hybridized carbons. In a molecule
XYCH2 [in which (X ≠Y), and neither X nor Y is H or D], replacement, separately, of each of the two
hydrogen atoms by D gives two enantiomers, and the hydrogens are said to be enantiotopic. Also
used for (b) molecules such as aldehydes, R1CHO, or certain ketones and alkenes. In ketones
R1R2CO (R1≠R2), addition of R3 (via a Grignard reagent) gives a pair of enantiomeric tertiary alcohols
depending on whether R3 has been added to the top or bottom face.
Endo(内侧的). A substituent on a bridge between bridgehead carbons in a bicyclic molecule that is on the
side of the larger bridge is said to be endo (see exo).
Enthalpy of atomization. ( hat) (原子化热)atomization enthalpy; heat of atomization.
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The change in enthalpy that occurs when one mole of a compound is converted into gaseous atoms.
All bonds in the compound are broken in atomization and none are formed, so enthalpies of
atomization are always positive.
Epimerization(差向异构化作用). A term used to denote the interconversion of two epimers.
Epimers(差向异构体). Diastereoisomers that differ in configuration at one of two or more stereogenic centres.
Equatorial bond( 平 伏 键 ). The six C–H bonds (or generally a C–X bond) of cyclohexane that are
approximately perpendicular to the three-fold axis of cyclohexane.(Chapter 1).
Equatorial(平伏的). The bonds in a chair cyclohexane that are oriented along the equator of the ring.
Erythro(赤式). A relative stereochemical term used for molecules that have two adjacent stereogenic centres
and with two substituents common to both centres. The name is taken from the four-carbon sugar
erythrose, oxidation of whose CH2OH and CHO groups to CO2H gives meso-tartaric acid.
Ester(酯) (R-CO2-R).
A molecule containing a carbonyl group adjacent to an oxygen (RCOOR'). Also a functional group.
An ester is a compound formed from an acid and an alcohol. In esters of carboxylic acids, the -COOH
group and the -OH group lose a water and become a -COO- linkage:
R-COOH + R'-OH = R-COO-R' + H2O
where R and R' represent organic groups.
Ether(醚) (C-O-C). A molecule containing oxygen singly-bonded to two carbon atoms. Also a functional
group. Ether often refers to diethyl ether.
Ethoxide（乙氧基金属；乙醇盐）(CH3CH2O-). anion formed by treating ethanol with an alkali metal.
Ethoxy group（乙氧基）(CH3CH2O-). A two carbon alkoxy susbtituent.
Ethyl alcohol（乙醇）(CH3CH2OH):.trivial name for ethanol.
Ethyl group（乙基）(CH3CH2-). A two carbon alkyl substituent.
to
Exo(向外的). Descriptors of the relative orientation of groups attached
non-bridgehead atoms in a bicyclo[x.y. z]alkane (x ≥ y > z >
0).
As
endo, except that the substituent is now on the side of the
smaller
bridge. These terms do not specify configuration in an
absolute
sense.
Fatty acid( 脂 肪 酸 )(RCOOH). Fatty acids are carboxylic acids with long
hydrocarbon side chains. Most natural fatty acids have hydrocarbon
chains
that don't branch; any double bonds occuring in the chain are cis isomers
(side
chains are attached on the same side of the double bond).
Ferric(铁离子). ferric ion. Deprecated. 1. the iron(III) ion, Fe3+. 2. A compound that contains iron in the +3
oxidation state.
Ferrous(亚铁离子). ferrous ion.
Deprecated. 1. the iron(II) ion, Fe2+. 2. A compound that contains iron in the +2 oxidation state.
-1
Fingerprint region(指纹区). Region of an IR spectrum below 1,500 cm . The fingerprint region of the IR
spectrum is often complex and difficult to interpret.
Fischer projection(费歇尔投影式). A method for diagrammatic representation of chiral molecules, chiefly in
conjunction with the D/L configuration convention. Used nowadays for sugars and amino acids.
Formaldehyde(甲醛) (HCHO). trivial name for methanal.
Formic acid (甲酸) (HCO2H). trivial name for methanoic acid.
Formula unit(分子单元). Compare with empirical formula. One formula weight of a compound.
Formula weight(分子量). formula mass. Compare with molecular weight and empirical formula. The formula
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weight is the sum of the atomic weights of the atoms in an empirical formula. Formula weights are usually
written in atomic mass units (u).
Free radical(自由基). A free radical is a molecule with an odd number of electrons. Free radicals do not have
a completed octet and often undergo vigorous redox reactions. Free radicals produced within cells can react
with membranes, enzymes, and genetic material, damaging or even killing the cell. Free radicals have been
implicated in a number of degenerative conditions, from natural aging to Alzheimer's disease.
Functional group(官能团).
A reactivity center. A substructure that imparts characteristic chemical behaviors to a molecule, for
example, a carboxylic acid group.
Functional isomers(官能团异构体).) compounds which have the same molecular formula that possess
different functional groups.
Gauche conformation(偏转构象). A type of staggered conformation in which two big groups are next to each
other. In the gauche conformation of butane, for example, the two methyl groups are related by a
dihedral angle of 60°.
Geminal(偕的). Adjective used to describe 1,1-disubstitution; for example, in dichloromethane (CH2Cl2) the
chlorines are geminal. In NMR spectroscopy a geminal coupling constant, 2J, occurs between nuclei
separated by two bonds.
Geometric isomer(几何异构体).
Geometric
isomers
have
different
configurations
at
a
double
bond,
e.g.
(E)-
and
(Z)-1,2-dichloroethene; in this context, cis/trans isomerism is also used.
Geometric isomers are molecules that have the same molecular formula and bond connections, but
distinctly different shapes.
Glycerol(甘油). (HOCH2CH(OH)CH2OH)
Glycerol is a small molecule with three alcohol groups. It is a basic building
block of
fats and oils.
Halide(卤化物). halide ion.
A member of the VIIA column of the periodic table (like F, Cl, Br, I, etc). Or a molecule that contains
one of these atoms. Also a functional group.
A compound or ion containing fluorine, chlorine, bromine, iodine, or astatine.
Halo group（卤素基团）(X-). substituent which is one of the four halogens; fluoro (F), chloro (Cl), bromo (Br),
or iodo (I).
Halogenation（卤化）. the addition of a halogen molecule (only Cl2 or Br2) to an alkene to produce an alkyl
dihalide or alkyne to produce an alkyl tetrahalide.
Helicity(螺旋性). The sense of twist of, say, a screw or helix. Defined as righthanded if, in proceeding along
the axis of the screw or helix, the sense of twist is clockwise.
Heteroatoms(杂原子；杂环原子). elements other than carbon and hydrogen that are commonly found in
organic molecules,such as nitrogen, oxygen and the halogens.
Heterocyclic(杂环的；异裂). heterocycle; heterocyclic ring.
Adjective used to describe the cleavage of a bond X–Y in which Y gains both bonding electrons to
give Y–, leaving X+.
An organic group or molecule containing rings with at least one noncarbon atom on the ring.
Homochiral(纯手性的). Molecules are homochiral if they possess the same sense of chirality, e.g. the
naturally occurring -amino acids which all have L configuration. Also used by some to denote enantiomeric
purity.
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Homolog(同系物). homologue; homologous; homologous series.
A compound belonging to a series of compounds that differ by a repeating group. For example,
propanol(CH3CH2CH2OH), n-butanol (CH3CH2CH2CH2OH), and n-pentanol (CH3CH2CH2CH2CH2OH)
are homologs; they belong to a homologous series CH3(CH2)nOH.
Homologous series( 同 系 列 ). compounds which differ only by the number of CH2 units present;
CH3CH2Cl,CH3CH2CH2Cl, and CH3CH2CH2CH2Cl, all belong to the same homologous series (1　alkyl
chlorides).
Homolytic bond cleavage(均裂). Occurs when a single bond between two atoms in A–B is broken so that
both A and B retain one of the bonding electrons.
Homotopic(等位). Adjective that can be used to describe a molecule that contains (a) sp3 hybridized carbons.
In, for example, CH2Cl2, separate replacement of each hydrogen by deuterium gives identical
molecules. The hydrogens are homotopic. Also used for molecules that contain (b) sp2 hybridized
carbons. In, for example, R1R2C=O, the carbonyl group is homotopic when R1 = R2. Addition of a
different R3 group (via a Grignard reagent) gives identical tertiary alcohols whether addition to the
carbonyl group occurs at the top or bottom face.
Hückel's rule(休克尔规则). A rule that states that completely conjugated planar rings with 4n+2 pi electrons
are aromatic.
Hybrid orbitals(杂化轨道). Orbitals formed from mixing together atomic orbitals, like the spx orbitals, which
result from mixing s and p orbitals.
Hybridization(杂化). A mathematical mixing of atomic orbitals (two or more in number) that gives the same
number of hybrid orbitals. The hybrid orbitals retain some of the properties of the component atomic
orbitals(see Table 1). Hybrid is from the Latin for ‘mongrel’.
Table 1 Characteristics of hybrid orbitals in methane, ethene and ethynea
a
A = number of s orbitals per molecule involved in forming hybrid orbitals. B = number of 2p orbitals
per molecule involved in forming hybrid orbitals. C = number and type of hybrid orbitals per molecule
formed after hybridization. D = number of p orbitals per molecule remaining after hybridization that
can be used to form multiple bonds, as in, say, alkenes and alkynes. E = bond angles at C, i.e.
∠HCH in methane, ∠HCC in ethene and ∠HCC in ethyne, respectively,after hybridization. Note
that for each row the sum of the entries in columns C and D is 4.
Hydrate(水合物；氢氧化物). Compare with addition compound.
A hydrate is an addition compound that contains water in weak chemical combination with another
compound. For example, crystals of CuSO4·5 H2O (copper sulfate pentahydrate) are made of
regularly repeating units, each containing 5 molecules of water weakly bound to a copper(II) ion and a
sulfate ion.
Hydration(水合；水合作用). the addition of a molecule of water to the carbon-carbon double bond of an
alkene to form an alcohol; the reaction follows Markovnikov’s rule and requires a mineral acid catalyst
(H+).
Hydrazine(肼). (NH2NH2)
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A colorless, fuming, corrosive liquid that is a powerful reducing agent. NH2NH2 is used in jet and
rocket fuels, and as an intermediate in the manufacture of agricultural, textile, photographic, and
industrial chemicals.
Hydrocarbon(烃；碳氢化合物). Compare with alkane, alkene, alkyne, and organic.
Hydrocarbons are organic compounds that contain only hydrogen and carbon. The simplest
hydrocarbons are the alkanes.
Hydrohalogenation（氢卤化作用；加上卤化氢）.the addition of a molecule of HCl or HBr to an alkene to form
an alkyl halide, or to an alkyne to form a geminal alkyl dihalide, the addition follows Markovnikov’s rule.
Hydrogen bond(氢键). hydrogen bonding.
An especially strong dipole-dipole force between molecules X-H...Y, where X and Y are small
electronegative atoms (usually F, N, or O) and ... denotes the hydrogen bond. Hydrogen bonds are
responsible for the unique properties of water and they loosely pin biological polymers like proteins
and DNA into their characteristic shapes.
Hydrolysis(水解). a substitution reaction in which a molecule of water replaces a leaving group in a
compound;examples would include the hydrolysis of ester or amides to the corresponding carboxylic
acids.
Hydronium ion(水合氢离子). (H3O+) hydronium.
The H3O+ ion, formed by capture of a hydrogen ion by a water molecule. A strong covalent bond is
formed between the hydrogen ion and water oxygen; all hydrogen ions in aqueous solution are bound
inside hydronium ions.
Hydroxide(氢氧化物；羟化物). (OH-) hydroxide ion. Compare with hydroxyl.
1. The OH- ion. 2. Compounds containing the OH- ion. See also: hydroxide compounds.
Hydroxyl group (羟基). (-OH)the functional group present in an alcohol.
Hygroscopic(吸湿的).
Able to absorb moisture from air. For example, sodium hydroxide pellets are so hygroscopic that they
dissolve in the water they absorb from the air.
Hygroscopicity(吸水性).
The ability of a substance to absorb moisture from air. For example, sodium hydroxide pellets are so
hygroscopic that they dissolve in the water they absorb from the air.
Hyperconjugation( 超 共 轭 效 应 ). Weak interaction (electron donation) between sigma bonds with p
orbitals. Hyperconjugation explains why alkyl substituents stabilize carbocations.
Incomplete octet(不完全八隅体).
1. An atom with less than eight electrons in its valence shell. 2. An atom with less than eight total
bonding and nonbonding electrons in a Lewis structure, for example, B in BH3 has an incomplete
octet.
Index of hydrogen deficiency (IHD，不饱和度): a basis for the comparison of the molecular formula of a
given compound to that of an acyclic alkane which has the same number of carbon atoms (since the latter
has the maximum number of hydrogens per carbon possible CnH2n+2); can be used to determine possible
structural formulas from a molecular formula; if the IHD = 1, the given compound may contain either 1 double
bond or 1 ring; if IHD =2, the compound may contain 2 double bonds, 2 rings, a ring and a double bond, or
one triple bond; etc.
Inductive effect(诱导效应). inductance effect.
Electron donation or withdrawal by electropositive or electronegative atoms through the sigma bond
framework.
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An inductive effect is the polarization of a chemical bond caused by the polarization of an adjacent
bond. (Field effects are polarization caused by nonadjacent bonds).
Inert pair(惰性电子对). inert pair effect.
Valence electrons in an s orbital penetrate to the nucleus better than electrons in p orbitals, and as a
result they're more tightly bound to the nucleus and less able to participate in bond formation. A pair of
such electrons is called an "inert pair". The inert pair effect explains why common ions of Pb are Pb4+
and Pb2+, and not just Pb4+ as we might expect from the octet rule.
Infrared spectroscopy(红外光谱法). IR spectroscopy.
A technique for determining the structure (and sometimes concentration) of molecules by observing
how infrared radiation is absorbed by a sample.
Inorganic chemistry(无机化学).
The study of inorganic compounds, specifically their structure, reactions, catalysis, and mechanism of
action.
Inorganic compound(无机化合物). inorganic. Compare with organic.
A compound that does not contain carbon chemically bound to hydrogen. Carbonates, bicarbonates,
carbides, and carbon oxides are considered inorganic compounds, even though they contain carbon.
Intermediate(中间体). Any species formed in a reaction on the way to making the product. Typically,
intermediates are unstable.
Ionic bond(离子键). ionically bound; ionic bonding. Compare with covalent bond.
An attraction between ions of opposite charge. Potassium bromide consists of potassium ions (K+)
ionically bound to bromide ions (Br-). Unlike covalent bonds, ionic bond formation involves transfer of
electrons, and ionic bonding is not directional.
Ionic compound(离子化合物). salt. Compare with covalent compound and ionic bond.
A compound made of distinguishable cations and anions, held together by electrostatic forces.
Ionic dissociation(离子离解). ionize; ionization.
When ionic substances dissolve, their ions are surrounded by solvent molecules and separated from
each other. This phenomena is also called ionization.
IR spectroscopy( 红 外 光 谱 ). An instrumental technique that measures IR light absorption by
molecules. Can be used to determine functional groups in an unknown molecule.
Isobutyl(异丁基). the (CH3)2CH-CH2- group, the trivial name for the 2-methylpropyl group.
Isochronous(等时的；同步的). In NMR spectroscopy, two or more nuclei are called isochronous if they have
the same chemical shift.
Isolated double bonds(隔离双键). Double bonds separated by more than one carbon-carbon single bond.
Isomers(异构体). compounds which have the same molecular formulas but different structures; they may be
sub-classified as functional, geometric, optical, positional, skeletal, stereo, or structural.
Isopropyl(异丙基). the (CH3)2CH- group, the trivial name for the 1-methylethyl group.
Isotactic(全规的；全同立构的). Term used to describe a polymer, e.g. polypropene, in which all the methyl
groups lie on the same side of the polymer chain (which is usually drawn in the plane of the paper).
IUPAC（国际纯粹与应用化学联合会）
International Union of Pure and Applied Chemistry, an organization which sets international standards
for chemical nomenclature, atomic weights, and the names of newly discovered elements.
J value(耦合常数值). The coupling constant between two peaks in an NMR signal.
Ketone(酮). (R-CO-R')
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An organic compound that contains a carbonyl group. For example, methyl ethyl A compound that
contains a carbonyl group attached to two carbons.
Also a functional group.
ketone is CH3COCH2CH3-is used in some adhesives.
Kinetic product(动力学产物). The product that forms the fastest. (This product has the lowest energy of
activation.)
Kinetic resolution(动力学拆分). Separation of enantiomers by means of a difference of reaction rate of the
enantiomers, e.g. with an enzyme (or an arti- ficial catalyst), in which case the rate difference is very
large. For example, a racemic ethanoate (acetate) can be hydrolysed to one enantiomer of an
alcohol; the other enantiomer remains as ethanoate.
Kinetics(动力学). The study of reaction rates.
Kw(水的质子自递常数；水的离子积). Kw.
Symbol for the autoprotolysis constant for water, equal to 1.01 × 10-14 at 25°C.
L-. L-isomer(L-异构体). Compare with D- .
Prefix used to designate a levorotatory enantiomer .
L-. L-isomer(L-异构体). Compare with D-.
Prefix used to designate a levorotatory enantiomer.
Laevorotatory (l)(左旋的 ). Description given to a chiral compound that rotates the plane of polarized light
anti-clockwise as the observer looks into the propagating beam.
Law of conservation of mass( 物质守恒定律).
There is no change in total mass during a chemical change. The demonstration of conservation of
mass by Antoine Lavoisier in the late 18th century was a milestone in the development of modern
chemistry.
Law of definite proportions( 定比定律).
When two pure substances react to form a compound, they do so in a definite proportion by mass.
For example, when water is formed from the reaction between hydrogen and oxygen, the 'definite
proportion' is 1 g of H for every 8 g of O.
Law of multiple proportions(倍比定律 ).
When one element can combine with another to form more than one compound, the mass ratios of
the elements in the compounds are simple whole-number ratios of each other. For example, in CO
and in CO2, the oxygen-to-carbon ratios are 16:12 and 32:12, respectively. Note that the second ratio
is exactly twice the first, because there are exactly twice as many oxygens in CO2 per carbon as there
are in CO.
Leaving group(离去基团). In a substitution or elimination reaction, the leaving group X in, say, R3C–X, leaves
with both the bonding electrons. Good leaving groups include I, Br, +OH2, 4-MeC6H4SO3 (OTs),
4-BrC6H4SO3(OBs).
Levorotatory(左旋的). Compare with dextrorotatory.
Having the property of rotating plane-polarized light counterclockwise.
Lewis acid(路易斯酸). An electron pair acceptor.
Lewis base(路易斯碱). An electron pair donor.
Lewis structure(路易斯结构). electron dot structure; dot structure.
A model pioneered by Gilbert N. Lewis and Irving Langmuir that represents the electronic structure of
a molecule by writing the valence electrons of atoms as dots. Pairs of dots (or lines) wedged between
atoms represent bonds; dots drawn elsewhere represent nonbonding electrons.
Ligand(配基).
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1. In inorganic chemistry, a molecule or ion that binds to a metal cation to form a complex. 2. In
biochemistry, a molecule that binds to a receptor, having a biological effect.
Litmus paper(石蕊试纸). litmus test.
Paper impregnated with litmus, usually cut in narrow strips. Dipping red litmus paper into a basic
solution turns it blue; dipping blue litmus paper into an acidic solution turns it red.
Litmus(石蕊).
A mixture of pigments extracted from certain lichens that turns blue in basic solution and red in acidic
solution.
Lone pair(孤电子对). nonbonding pair; unshared pair.
Electrons that are not involved in bonding.
Markovniknov’s rule(马尔科夫尼科夫规则). A rule that states that electrophiles add to the less highly
substituted carbon of a carbon-carbon double bond (or the carbon with the most hydrogen atoms).
Mass spectrometry( 质 谱 法 ). An instrumental technique involving the ionization of molecules into
fragments. Can be used to determine the molecular weights of unknown molecules.
Mechanism(机理). The step-wise molecular processes by which a reaction proceeds. Understanding the
mechanism of a reaction allows generalizations and predictions to be made about the outcome of
similar reactions. Mechanisms are always postulated. Mechanisms must be consistent with product
analysis and kinetic information.
Meso compounds(内消旋化合物). Molecules that have chiral centers but are achiral as a result of one or
more planes of symmetry in the molecule.
Meso(内消旋). A name given to an achiral stereoisomer of a family of diastereoisomers. A meso stereoisomer
is achiral by virtue of two selfcancelling stereogenic centres.
Meta(间位). Describes the positions of two substituents on a benzene ring that are separated by one carbon.
Meta-directing substituent(间位定位基 ). Any substituent on an aromatic ring that directs in coming
electrophiles to the meta position.
Methoxy group (甲氧基). (CH3O-) the simplest alkoxy substituent.
Methyl(甲基). (-CH3)
A group -CH3, derived from methane. For example, CH3Cl is "methyl chloride" (systematic name:
chloromethane); CH3OH is "methyl alcohol" (systematic name: methanol).
Methyl alcohol(甲醇). (CH3OH) trivial name for methanol.
Mixed glyceride(混酸甘油酯). Compare with glyceride.
A diglyceride or triglyceride that contains more than one type of fatty acid connected to glycerol via
an ester linkage. Natural oils and fats usually contain several different mixed glycerides.
Molecular formula(分子式). formula; chemical formula. Compare with empirical formula.
A notation that indicates the type and number of atoms in a molecule. The molecular formula of
glucose is C6H12O6, which indicates that a molecule of glucose contains 6 atoms of carbon, 12 atoms
of hydrogen, and 6 atoms of oxygen.
Molecular geometry(分子几何结构).
1. The three-dimensional shape of a molecule. For example, methane (CH4) has a tetrahedral
molecular geometry. 2. The study of molecular shapes.
Molecular ion(分子离子). The fragment in a mass spectrum that corresponds to the cation radical (M+)of the
molecule. The molecular ion gives the molecular mass of the molecule.
Molecular model(分子模型). stick model; ball and stick model; spacefilling model.
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A representation of a molecule. The model can be purely computational or it can be an actual physical
object. Stick models show bonds, ball-and-stick models show bonds and atoms, and spacefilling
models show relative atomic sizes.
Molecular orbital theory(分子轨道理论). Model for depict ing the location of electrons that allows electrons to
delocalize across the entire molecule. A more accurate but less user-friendly theory than the
valence-bond model.
Molecular orbital(分子轨道). Compare with atomic orbital and orbital. A wavefunction that describes the
behavior of an electron in a molecule. Molecular orbitals are usually spread across many atoms in
the molecule, and they are often described as a combination of atomic orbitals on those atoms.
Molecular sieve(分子筛). A material that contains many small cavities interconnected with pores of precisely
uniform size. Zeolites are an example. Molecular sieves adsorb molecules that are small enough to
pass through their pore systems- especially water. They are often used as drying agents, and to
separate large molecules from smaller ones in preparatory work and in exclusion chromatography.
Molecular weight(分子量). molecular mass. Compare with formula weight and molecular formula. The
average mass of a molecule, calculated by summing the atomic weights of atoms in the molecular
formula. Note that the words mass and weight are often used interchangeably in chemistry.
Monodentate(单配位基). A ligand that has only one atom that coordinates directly to the central atom in a
complex. For example, ammonia and chloride ion are monodentate ligands of copper in the
complexes [Cu(NH3)6]2+ and [CuCl6]2+.
Multiple bond(重键). Sharing of more than one electron pair between bonded atoms. A double bond consists
of two shared pairs of electrons; a triple bond consists of three shared pairs.
Multistep synthesis(多步合成).
Mutarotation(变旋现象). The change in optical rotation accompanying epimerization. In sugar chemistry this
term usually refers to epimerization at the hemiacetal carbon atom.
n+1 rule(n+1规则). Rule for predicting the coupling for a proton = in 1H NMR spectroscopy. An NMR signal
will split into n+1 peaks, where n is the number of equivalent adjacent protons.
Natural product(天然产物). A compound produced by a living organism.
Neutral(中性 ). 1. having no net electrical charge. Atoms are electrically neutral; ions are not. 2. A solution
containing equal concentrations of H+ and OH-.
Neutralization reaction(中和反应). neutralization; acid-base reaction. A chemical change in which one
compound aquires H+ from another. The compound that receives the hydrogen ion is the base; the
compound that surrenders it is an acid.
Newman projection (see Chapter 1)( 纽曼投影式).
Nitric acid. (HNO3) aqua fortis(硝酸 ). A corrosive liquid with a sharp odor that acts as a strong acid when
dissolved in water. Nitric acid is used to synthesize ammonium nitrate for fertilizers, and is also used in the
manufacture of explosives, dyes, and pharmaceuticals. Salts of nitric acid are called nitrates.
Nitrile(腈). Compounds having the structure RCΞN; thus C-substituted derivatives of hydrocyanic acid, HCΞN.
In systematic nomenclature, the suffix nitrile denotes the triply bound ΞN atom, not the carbon atom attached
to it.
NMR(核磁共振). Nuclear magnetic resonance sprectroscopy. A technique th at measures radiofrequency
light absorption by molecules. A powerful structure-determining method.
Node(节点). A region in an orbital with zero electron density.
Nomenclature(命名法 ).
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A system for naming things. For example, "organic nomenclature" is the system used to name
organic compounds.
Nucleophile (from the Greek, ‘nucleus loving’)( 亲核试剂). Nucleus lover. A molecule with the ability to
donate a lone pair of electrons (a Lewis base)
Nucleophilicity(亲核性). A measure of the reactivity of a nucleophile in a nucleophilic substitution reaction.
OBs(4-甲基苯磺酸盐). See Brosylate (4-bromobenzenesulfonate, 4-BrC6H4SO3), above.
Octane(辛烷). (C8H18) Compare with alkane and hydrocarbon . Flammable liquid compounds found in
petroleum and natural gas. There are 18 different octanes- they have different structural formulas but share
the molecular formula C8H18. Octane is used as a fuel and as a raw material for building more complex
organic molecules. It is the eighth member of the alkane series.
Octet rule(八隅规则). A guideline for building Lewis structures that states that atoms tend to gain, lose, or
share valence electrons with other atoms in a molecule until they hold or share eight valence electrons. The
octet rule almost always holds for carbon, nitrogen, oxygen, and fluorine; it is regularly violated for other
elements.
Octet(八隅体；八重态). A set of eight valence electrons.
Olefin(石蜡). another name for an alkene.
Optical activity(旋光性). A substance that is capable of rotating plane-polarized light. Molecules of an
optically active substance cannot be superimposed on their own mirror images, just as your left hand cannot
be superimposed on your right when both are held palm-down.
Optical isomers(光学异构体). this refers to compounds which will rotate the plane of polarized light by the
same amount, but in opposite directions; also called enantiomers (i.e. non-superimposable mirror images).
Optically active compound(旋光性活性化合物). A compound, necessarily chiral, and non-racemic, that
rotates the plane of polarized light in a particular direction.
Optically pure(光学纯的). Mainly superseded by ‘enantiomerically pure’.
Orbital(轨道). The region of space in which an electron is confined (the electron “apartment”).
Organic chemistry(有机化学). The study of compounds that contain carbon chemically bound to hydrogen,
including synthesis, identification, modelling, and reactions of those compounds.
Organic compound(有机化合物). Carbon-containing compound.
Organic(有机的 ). organic compound. Compare with inorganic compound.
Compounds that contain carbon chemically bound to hydrogen. They often contain other elements
(particularly O, N, halogens, or S). Organic compounds were once thought to be produced only by
living things. We now know that any organic compound can be synthesized in the laboratory
(although this can be extremely difficult in practice!)
Ortho(邻位的). Describes the positions of two substituents on a benzene ring that are on adjacent carbons.
Orthogonal(直角的；正交的).
Ortho-para director(邻、对位定位基). An aromatic substituent that directs incoming electrophiles to the ortho
or para positions.
OTs( ). See Tosylate (toluene-4-sulfonate, 4-MeC6H4SO3), below.
Oxidation( 氧 化 ). a reaction in which electrons are lost by a species or molecule; also the gain of
carbon-oxygen bonds, and/or loss of carbon-hydrogen bonds e.g. 1-butanol→butanal → butanoic acid.
Para(对位的). Describes the poitions of two substituents on a benzene ring that are separated by two
carbons.
Paraffin(n.石蜡；vt.涂以石蜡). paraffin wax. 1. a waxy substance that is a mixture of alkanes with chains
containing 18 to 36 carbon atoms. 2. An alkane.
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Pericyclic reactions(周环反应). A chemical reaction in which concerted reorganization of bonding place
throughout a cyclic array of continuously bonded atoms. It viewed as a reaction proceeding through a
fully conjugated cyclic transition state. The number of atoms in the cyclic array is usually six, but
numbers are also possible. The term embraces a variety of processes, including cycloadditions,
cheletropic reactions, electrocyclic reactions sigmatropic rearrangements, etc. (provided they are
concerted).
pH (表示氢离子活度的) pH is a measure of effective concentration of hydrogen ions in a solution. It is
approximately related to the molarity of H+ by pH = - log [H+]
Phenol(酚). A group or molecule containing a benzene ring that has a hydroxyl group substituted for a ring
hydrogen.
Phenolphthalein(酚酞). An organic compound used as an acid-base indicator. The compound is colorless in
acidic solution and pink in basic solution (with the transition occuring around pH 8.3). Phenolpthalein
was used for many years as a laxative in very low concentrations- high concentrations are toxic!
Phenyl. (苯基) (C6H5- or Ph-) phenyl ring(苯环). A benzene ring as a substituent. Abbreviated Ph. A
molecular group or fragment formed by abstracting or substituting one of the hydrogen atoms attached
to a benzene ring.
Pi bond(π键). (
bond) Compare with sigma bond.
In the valence bond theory, a pi bond is a valence bond formed by side-by-side overlap of p orbitals
on two bonded atoms. In most multiple bonds, the first bond is a sigma bond and all of the others are
pi bonds.
pKa:The scale for defining a molecule's acidity (pKa =-log Ka).
Plane of symmetry(对称面). A plane cutting through a molecule in which both halves are mirror images of
each other. The presence of a plane of symmetry in a molecule means that it can be superimposed
on its mirror image. Molecules with a plane of symmetry, in any conformation, cannot be chiral.
Plane polarized light(平面偏振光). Light that oscillates in a single plane.
Light that emerges from a polarizer, which acts as a filter to block the light waves other than those
oscillating in a single plane. An integral part of a polarimeter, and very important to detection of
chirality.
Polar bond(极性键). Compare with covalent bond and ionic bond.
A bond involving electrons that are unequally shared. Polar bonds can be thought of as intermediate
between the extremes represented by covalent bonds and ionic bonds.
Polar molecule(极性分子). polar. Compare with covalent compound, ionic compound and polar bond. An
asymmetric molecule containing polar bonds. H2O, NH3, and HCl are examples of polar molecules.
Non-examples are CO2, CCl4, and BCl3 which contain polar bonds but are nonpolar because they have
symmetric shapes. Alkanes are usually asymmetric but are nonpolar because they contain no polar
bonds. Polar molecules are electric dipoles and they attract each other via dipole-dipole forces.
Polarimeter(偏振器；旋光计). An instrument for determination of the number of degrees by which a particular
sample of a chiral compound rotates the plane of polarized light. This enables the specific rotation (see
below) to be calculated.
Polyatomic ion(多原子离子). Compare with molecule, ion and polyatomic molecule. A polyatomic ion is a
charged particle that contains more than two covalently bound atoms. See Polyatomic Ions for more.
Polyatomic molecule(多原子分子). Compare with polyatomic ion and diatomic molecule. A polyatomic
molecule is an uncharged particle that contains more than two atoms.
Polydentate(多配位基的). polydentate ligand. A ligand that has more than one atom that coordinates directly
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to the central atom in a complex. Polydentate ligands are called chelating agents when two or more
coordinating atoms are attached to the same metal ion in a complex. For example, EDTA or
ethylenediaminotetracetic acid is a hexadentate ligand of calcium ion.
Polymer(高分子化合物). A large molecule made by linking smaller molecules ("monomers") together.
Positional isomers(位置异构体). compounds which differ only in the position of a functional group;
2-pentanol and 3-pentanol are positional isomers.
Primary (1级的，伯；第一位的；主要的) general term used to describe a specific structural arrangement in
which a carbon atom is attached to one other carbon atom.
primary alcohol (RCH2OH): alcohol in which the OH group is bonded to a carbon bonded to one alkyl group.
primary amine (RNH2): amine in which the N atom is bonded to one alkyl group.
Propane.(C3H8) (丙烷) Compare with alkane and hydrocarbon. A colorless, odorless, flammable gas, found
in petroleum and natural gas. It is used as a fuel and as a raw material for building more complex
organic molecules. Propane is the third member of the alkane series.
Propoxy group(丙氧基). (CH3CH2CH2O-) a straight chain three carbon alkoxy substituent.
Propyl group (丙基). (CH3CH2CH2-) a straight chain three carbon alkyl substituent.
Protic solvent(质子溶剂). A solvent that contains O-H or N-H bonds.
Proton donor(质子供体). acid. Compare with base. Because a free H+ ion is technically a bare proton, acids
are sometimes referred to as "proton donors" because they release hydrogen ions in solution. The
term "proton donor" is misleading, since in aqueous solution, the hydrogen ion is never a bare protonit's covalently bound to a water molecule as an H3O+ ion. Further, acids don't "donate" protons; they
yield them to bases with a stronger affinity for them.
Proton(质子). An H+ ion. Also a positively-charged nuclear particle.
Qualitative analysis(定量分析). visual tests used in the laboratory to determine the presence or absence of a
given functional group:
Beilstein Test: the appearance of a green flame when a sample of an organic compound is burned on a
copper wire is indicative of the presence of an alkyl halide.
Brady’s Test: the formation of a yellow or orange precipitate when an organic compound is treated with
Brady’s reagent is indicative of the presence of an aldehyde or a ketone.
Bromine Test: the formation of a colourless solution when an organic compound is treated with a solution of
bromine (orange-brown) is indicative of the presence of an unsaturated hydrocarbon(alkene or alkyne).
KHCO3 Test: the rapid formation of bubbles of CO2 when an organic compound is treated with KHCO3(aq) is
indicative of the presence of a carboxylic acid.
KMnO4 Test: the formation of a brown precipitate when an organic compound is treated with a basic solution
of potassium permanganate (purple solution) is indicative of the presence of a functional group which
can be oxidized (an alkene, alkyne, aldehyde, primary or secondary alcohol).
Lucas Test: the rapid formation of a milky suspension when an organic compound is treated with the Lucas
reagent is indicative of the presence of a tertiary alcohol; secondary alcohols react much slower, and
primary alcohols hardly at all.
Sodium Test: the evolution of hydrogen gas when an organic compound is treated with sodium metal is
indicative of the presence of an alcohol or a carboxylic acid.
Tollens’ Test: the formation of a silver mirror when an organic compound is treated with Tollens’ reagent is
indicative of the presence of an aldehyde.
Quaternary (4　) carbon(季碳原子). a carbon that is bonded to four carbon atoms.
R group(R基). Abbreviation given to an unimportant part of a molecule. Indicates Rest of molecule.
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Racemate(消旋体). A sample that consists of a 1:1 ratio of enantiomers.
Racemic(外消旋的 ). racemic mixture(外消旋混合物). A 50:50 mixture of two enantiomers. Racemic
mixtures are optically inactive (don't rotate plane-polarized light). A mixture of equal parts of the
levorotatory
and dextrorotatory
isomers of the the same substance. Racemic mixtures are not
optically active .
Racemization(外消旋化作用). Racemization is the conversion of one enantiomer into the racemate.
Radical(根; 原子团; 基). An atom or molecule with an unpaired electron.
Rate-Limiting Step(速率限制步；决定速率步). This is the slowest step in a multi-step reaction mechanism. In
can be thought of as a "bottle-neck" of the reaction, in the sense that the overall reaction cannot
proceed any faster than the slowest step will allow.
Reduction(还原). a reaction in which a substance gains electrons, or loses O atoms, or gains H atoms;
examples would be: Cl2 H 2Cl-, and the conversion of 2-butanone to 2-butanol.
Regioselective(区域选择性). When, for example, a reagent XY adds to a double bond R1R2C=CR3R4, two
products can be formed: R’R2CX–CR3R4Y and R1R2CY–CR3R4X. If one isomer predominates over the
other, the reaction is called regioselective.
Resolution(拆分；分辨本领; 分离度). Separation of a 50:50 mixture of enantiomers in order to obtain one, or
both, enantiomers.
Resonance(共振 ). resonance effect(共振效应). mesomeric effect. Description of the ground state of a
molecule with delocalized electrons as an average of several Lewis structures. The actual ground state
doesn't switch rapidly between the separate structures: it is an average. If electron density at a
particular point in a molecule is higher or lower than what you'd expect from a single Lewis structure,
and various canonical structures can be drawn to show how electron delocalization will explain the
discrepancy, the difference in electron density is called a "resonance effect" or "mesomeric effect".
Resonance structures(共振结 构). Structures used to better depict the location of pi and nonbonding
electrons on a molecule. A molecule looks like a hybrid of all resonance structures.
Road map(路线图). a type of question in which the structures of the compounds must be deduced from the
formulas of the compounds and the results of various reactions.
Saturated(饱和的). a compound which does not contain any double or triple bonds.
Saponification(皂化). The base catalzed hydrolysis of esters to yield carboxylates and an alcohol. The term
comes from ‘soap making’.
Sawhorse projection(锯架投影式). An oblique view of a carbon–carbon single bond that enables the
observer to see the stereochemistry of substituents. Three substituents are connected to each carbon
by a stick diagram that resembles a Y (the Y can rotate). Introduced in Chapter 1.
Scalemic(部分消旋的). Any non-racemic chiral substance. A scalemic sample is one that is partially
racemized (or enantiomerically enriched).
s-cis conformation(s-顺式构象). A conformation in which the two double bonds of a conjugated diene are
on the same side of the carbon-carbon single bond that connects them. The required conformation for
the Diels-Alder reaction.
Secondary (2级的，仲的；第二的；次要的) general term used to describe a specific structural arrangement in
which a carbon atom that is attached to two other carbon atoms.
secondary alcohol (R2CH-OH) alcohol in which the OH group is bonded to a carbon atom bonded to two
alkyl groups.
secondary amine (R2NH) amine in which the N atom is bonded to two alkyl groups.
Side chain(侧链；支链). a chain of atoms which is attached to a longer chain of atoms; examples of side
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chains would be methyl, ethyl, propyl groups (among others).
Sigma bond(σ键). (
bond) Compare with pi bond. In the valence bond theory, a sigma bond is a valence
bond that is symmetrical around the imaginary line between the bonded atoms. Most single bonds are
sigma bonds.
Singlet(单峰，单线态). Describes an NMR signal consisting of only one peak.
Skeletal isomers(碳胳异构体). isomers which differ in the length of the carbon chain; examples are pentane
and dimethylpropane.
sp(sp杂化轨道). A hybrid orbital made by mixing one s orbital and one p orbital.
sp2(sp2杂化轨道 ). A hybrid orbital made by mixing one s orbital and two p orbitals.
sp3, sp2 and sp orbitals(sp3, sp2 和sp杂化轨道 ). Hybrid orbitals derived by mathematical mixing of one sand n p-orbitals (where n = 1, 2 or 3) to give (n + 1) hybrid orbitals. Any remaining unhybridized
p-orbitals can be used to form multiple bonds, as in alkenes and alkynes.
3
sp (sp3杂化). A hybrid orbital made by mixing one s orbital and three p orbitals.
Specific rotation( 比旋光度), e.g. [α] 25
D . The number of degrees (+ or –) by which a solution of a
non-racemic chiral compound rotates the plane of polarized light, under conditions of (a) unit
concentration and (b) unit path length of cell; by convention, the degree symbol is not shown.
Dextrorotatory compounds are assigned (+). For determinations of liquids, density is used for c in
equation 1 of Chapter 2. The superscript 25 refers to the temperature in degrees centigrade, and the
subscript D to the wavelength of the light, usually the sodium D line.
Staggered conformation(交叉式构象). Conformation about a carbon-carbon single bond in which bonds off
of one carbon are at a maximum distance apart from bonds coming off of an adjacent carbon (60odg
apart when viewed in a Newman projection).
Stereochemistry( 立体化学). Study of molecules in three dimensions.
Stereogenic centre (Chiral centre, Asymmetric centre)( 手性中心、不对称中心).
Stereoisomers(立体异构体). Isomers that differ only in the spatial orientation of their component atoms. a
type of isomer where the molecules have the same connectivity, except for the arrangement of those
bonds in space.
Stereoselectivity(立体选择性). The selectivity of a reaction for forming one stereoisomer of a product in
preference to another stereoisomer.
Stereospecific(立体特异性). exhibiting marked specificity for one of several stereoisomers of a substrate or
reactant; said of enzymes or of synthetic organic reactions. A reaction is termed stereospecific if
starting materials differing only in their configuration are converted into stereoisomeric products.
According to this definition, a stereospecific process is necessarily stereoselective but not all
stereoselective processes are stereospecific. Stereospecificity may be total (100%) or partial. The term
is also applied to situations where reaction can be performed with only one stereoisomer. For example,
the exclusive formation of trans-1,2-dibromocyclohexane upon bromination of cyclohexene is a
stereospecific process, although the analogous reaction with (E)-cyclohexene has not been performed.
Steric hindrance(位阻). The original term for a steric effect arising from crowding of substituents.
Stereochemistry(立体化学). the branch of organic chemistry that deals with the three-dimensional structure
of molecules.
Stereogenic carbon (asymmetric carbon) (立体碳原子；不对称碳原子；手性碳原子). a carbon atom which is
bonded to four different groups or atoms; a chiral molecule must contain a stereogenic carbon, and
therefore has no plane of symmetry and is not superimposable on its mirror image.
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Stereoisomers( 立 体 异 构 体 ).isomers which have the same bonding connectivity but have a different
three-dimensional structure; examples would be cis-2-butene and trans-2-butene (geometric isomers),
and the left and right handed forms of 2-butanol (enantiomers).
Stoichiometry(化学计量学). 1. Ratios of atoms in a compound. 2. Ratios of moles of compounds in a reaction.
3. A branch of chemistry that quantitatively relates amounts of elements and compounds involved in
chemical reactions, based on the law of conservation of mass and the law of definite proportions.
s-trans conformation(s-反式构象).
Strong acid(强酸). Compare with weak acid.
A strong acid is an acid that completely dissociates into hydrogen ions and anions in solution. Strong
acids are strong electrolytes. There are only six common strong acids( ). HCl (hydrochloric acid), HBr
(hydrobromic acid), HI (hydroiodic acid), H2SO4 (sulfuric acid), HClO4 (perchloric acid), and HNO3
(nitric acid).
Strong base(强碱).
A strong base is an base that completely dissociates into ions in solution. Strong bases are strong
electrolytes. The most common strong bases are alkali metal and alkaline earth metal hydroxides.
Strong ligand(强配位基). strong field ligand. Compare with weak ligand.
A ligand that causes a large crystal field splitting which results in a low-spin complex.
Structural formula(结构式). Compare with molecular formula and empirical formula.
A structural formula is a diagram that shows how the atoms in a molecule are bonded together. Atoms
are represented by their element symbols and covalent bonds are represented by lines. The symbol
for carbon is often not drawn. Most structural formulas don't show the actual shape of the molecule
(they're like floor plans that show the layout but not the 3D shape of a house).
Structural Isomer(结构异构体；构造异构体). A molecule which has the same molecular formula but a
different structure.
Substituent(取代基). an atom or group of atoms that is attached to a group of atoms; examples would be
Cl-(chloro), NO2- (nitro), CH3CH2- (ethyl), etc...
Substitution reaction(取代反应；置换反应). process in which one group or atom in a molecule is replaced by
another group or atom.
SN1 reaction(单分子亲核取代反应). A first order substitution reaction that goes through a carbocation
intermediate.
SN2 reaction(双分子亲核取代反应). A second order substitution reaction that takes place in one step and has
no intermediates.
Sugar(糖). A carbohydrate with a characteristically sweet taste. Sugars are classified as monosaccharides,
disaccharides, or trisaccharides.
Superoxide(过氧化物). superoxide ion(过氧化物离子). A binary compound containing oxygen in the -½
oxidation state. For example, KO2 is potassium superoxide, an ionic compound containing the
superoxide ion, O2-.
Suprafacial(同侧的).
Syn( 希腊字头，顺式；同；共) (see also Syn addition; Syn periplanar).
Syn addition(顺式加成).
Syn clinal(顺错构象，sc).
Syn periplanar(顺式共平面).
Syndiotactic(异位的).
Tautomer(互变异构体).
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理学院应用化学系有机化学教研室
A structure formed by facile motion of a hydrogen from one site to another within the same molecule.
Tautomers(互变异构体). Tautomerism(互变异构现象). Molecules that differ in the placement of a hydrogen
and double bonds and are easily interconvertible. Keto and enol forms are tautomers. Isomerism
brought about by rapid and reversible interconversion of, say, a ketone with an -hydrogen and an
enol, as inR12CH–C(=O)R2 and R12C=C(OH)R2. The conversion is usually acid orbase catalysed. The
keto form is usually more stable, though not when a phenol is the ‘enol’.
Thermodynamic product(热力学产物). The reaction product with the lowest energy..
Thermodynamics(热力学). Study of the energies of molecules.
Tert (t-叔的；第三位的): prefix used to indicate that the carbon atom connected to the main chain of a
molecule is itself bonded to three carbon atoms: (CH3)3C- is the t-butyl group. This prefix is not counted
for alphabetization purposes.
Tert-butyl (t-butyl) (叔丁基). trivial name for the 1,1-dimethylethyl group.
Tertiary (3级的，叔的；第三位的): general term used to describe a specific structural arrangement.
tertiary alcohol (R3C-OH)an alcohol in which the OH group is bonded to a carbon atom bonded to three alkyl
groups.
tertiary amine (R3N): an amine in which the N atom is bonded to three carbon atoms.
Thin layer chromatography(薄层色谱). (TLC) Compare with chromatography. A technique for separating
components in a mixture on the basis of their differing polarities. A spot of sample is placed on a flat
sheet coated with silica and then carried along by a solvent that soaks the sheet. Different components
will move different distances over the surface. TLC is a useful screening technique in clinical chemistry;
for example, it can be used to detect the presence of drugs in urine.
Thiol(硫醇). A molecule containing an SH group. Also a functional group.
Thio-(含硫的 ). A prefix that means, "replace an oxygen with sulfur". For example, sulfate ion is SO42-;
thiosulfate ion is S2O32-. Cyanate ion is OCN-; thiocyanate ion is SCN-.
main
Threo(苏式). The relative configuration at two contiguous carbon atoms in the
chain bearing, respectively, substituents a and b (a≠b), is designated
by
prefix erythro or threo, as appropriate, by analogy with the terminology
the
for
carbohydrate systems in which the substituents are OH.
Toluene (C6H5CH3) trivial name for methylbenzene
Torsion barrier(扭转位阻).
Tosylate (toluene-4-sulfonate, 4-MeC6H4SO3)(对甲基苯磺酸盐).
Trans(反式).
species
Transition state(过渡态). The highest point on the energy hill that takes one
into another.
Triglyceride(甘油三酸酯). A triglyceride is an ester of glycerol and three fatty
acids . Most
animal fats are composed primarily of triglycerides. In the structures below,
the fatty acids
attached to the glycerol are represented by 'R'. The fatty acids can be the
same
or
different.
Triple bond. ( ).(叁键) A covalent bond that involves 3 bonding pairs. In the valence bond theory, one of the
T
bonds in a triple bond is a sigma bond and the other two are pi bonds. For example, the central bond
in acetylene is a triple bond: H-C C-H.
Triplet(三重). Describes an NMR signal split into three peaks.
Trivial name(俗名). common name which has been used for a long period of time for a simple compound, or
a simple common name for a very complicated structure. The structural formula cannot be deduced
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from the name using a set of rules.
Unit of unsaturation(不饱和单元). also called the index of hydrogen deficiency (IHD).
Unsaturated (不饱和的). refers to a compound which contains at least one double or triple bond; addition of
excess hydrogen to such a molecule will produce a saturated compound.
Unsaturated compound(不饱和化合物). An organic compound with molecules containing one or more
double bonds.
Valence bond(价键). In the valence bond theory, a valence bond is a chemical bond formed by overlap of
half-filled atomic orbitals on two different atoms.
Valence electron(价电子). Electrons that can be actively involved in chemical change; usually electrons in
the shell with the highest value of n. For example, sodium's ground state electron configuration is 1s2
2s2 2p6 3s1; the 3s electron is the only valence electron in the atom. Germanium (Ge) has the ground
state electron configuration 1s2 2s2 2p6 3s2 3p6 3d10 4s2 4p2; the 4s and 4p electrons are the valence
electrons.
Valence shell(价电子层). The shell corresponding to the highest value of principal quantum number in the
atom. The valence electrons in this shell are on average farther from the nucleus than other electrons;
they are often directly involved in chemical reaction.
Valence(价 ). The number of hydrogen atoms that typically bond to an atom of an element. For example, in
H2O, oxygen has a valence of 2; carbon in CH4 has a valence of four.
Van der Waals’ radius(范德华力作用半径).
Vicinal(邻近的).
Water gas(水煤气). blue gas（蓝煤气，氰毒气）; synthesis gas(合成气). A fuel gas used in industrial
synthesis of organic chemicals, and in welding, glassmaking, and other high-temperature industrial
applications. Water gas made by passing steam over a bed of hot coal or coke. It consists mainly of of
carbon monoxide (CO) and hydrogen (H2), contaminated with small amounts of CO2, N2, CH4, and O2.
Water of crystallization(结晶水). water of hydration. Water that is stoichiometrically bound in a crystal; for
example, the waters in copper sulfate pentahydrate.
Wax(蜡；蜡状物). An ester formed from long-chain fatty acids and alcohols that is usually solid at room
temperature.
Weak acid(弱酸). Compare with strong acid. An acid that only partially dissociates into hydrogen ions and
anions in solution. Weak acids are weak electrolytes. Recognize weak acids by learning the six
common strong acids; any acid that doesn't appear on the list of strong acids is usually a weak acid.
Weak base(弱碱). Compare with strong base. A base that only partially dissociates into ions in solution.
Weak bases are weak electrolytes. Ammonia is an example of a weak base; the reaction NH3(aq) +
H2O(l) = NH4+(aq) + OH-(aq) is reversible.
Weak ligand( 弱配位基). weak field ligand. Compare with strong field ligand. A ligand that causes a small
crystal field splitting which results in a high-spin complex.
-yl(-基). A suffix indicating a molecular fragment or group; e. g. a methyl group (-CH3) derived from methane
(CH4).
Z isomer(Z异构体). Isomer in which the two highest-priority substituents are on the same side of a double
bond or ring.
Zwitterion( 两性离子). A particle that contains both positively charged and negatively charged groups. For
example, amino acids (NH2-CHR-COOH) can form zwitterions (+NH3-CHR-COO-)
相关 IUPAC 化学名词和概念请参看：
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理学院应用化学系有机化学教研室
http://www.iupac.org/publications/compendium/index.html
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有机化学常见概念中英对照
中文名称
英文名
β-酮酸酯
β-ketone ester
DL 规则
DL convention
D-异构体
D-isomer
E-异构体
E isomer
L-异构体
L-isomer
n+1 规则
n+1 rule
π键
pi bond
R/S 构型命名法
Cahn–Ingold–Prelog (CIP) R/S convention
R基
R group
s-反式构象
s-trans conformation
α,β-不饱和酮
α,β-unsaturated ketone
σ键
sigma bond
氨、氨水
ammonia(NH3)
氨基
amino group
氨基酸
amino acid
氨络物
ammine
铵根离子
ammonium ion(NH4+) ammonium.
胺
amine
螯合物
chelate
八隅规则
octet rule
半缩醛
hemiacetal
半缩酮
hemiketal
饱和脂肪族烃
saturated aliphatic hydrocarbon
苯
benzene
苯环
phenyl ring
苯基
phenyl group
苯炔; 脱氢苯
benzyne
苄基；苯甲基
benzyl group
变性
denaturation
变旋
Mutarotation
氢离子活度的 pH 值
pH
丙二烯
Allenes
丙烷
propane
薄层色谱
thin layer chromatography(TLC)
不饱和烃
unsaturated hydrocarbon
不规则的
Atactic
不完全八隅体
incomplete octet
布朗斯特碱
Brösted base
布朗斯特酸
Brösted acid
部分消旋的
Scalemic
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理学院应用化学系有机化学教研室
差向异构化作用
Epimerization
差向异构体
Epimers
拆分; 分辨率; 分离度
Resolution
超共轭; 超共轭效应
hyperconjugation
稠环芳烃
condensed aromatics
船式构象
Conformation (boat)
纯手性; 纯手性的
Homochiral
醇
alcohol(ROH)
醇酸
alcoholic acid
醇盐
alkoxide(RO- M+) alkoxide ion.
醋酸盐
acetate
单分子亲核取代反应
SN1 reaction
单分子消除反应
E1 elimination reaction
单配位基
monodentate
蛋白质
protein
等时的；同步的
Isochronous
等位; 等位的;
Homotopic
狄尔斯-阿尔德反应
Diels-Alder reaction
电负性
electronegativity
电环化反应、π-键环化反应
Electrocyclic reactions
电价键; 离子键
ionic bond
电偶极矩
electric dipole moment(µ)
电偶极子
electric dipole
淀粉
starch
动理学; 动力学
kinetics
动力学拆分
Kinetic resolution
动力学产物
kinetic product
对
para
对称面
Plane of symmetry
对甲基苯磺酸盐
Ots，Tosylate (toluene-4-sulfonate, 4-MeC6H4SO3)
对溴苯磺酸盐
OBs，Brosylate (4-bromobenzenesulfonate, 4-BrC6H4SO3),
对旋
Disrotatory
对映体
Enantiomers
对映体过量百分数
Enantiomeric excess; enantiomeric ratio
对映体过量的
Enantiomerically enriched
对映异位的
Enantiotopic
非质子溶剂
aprotic solvent
多步合成
multistep synthesis
多配位基的
polydentate
多原子分子
polyatomic molecule
多原子离子
polyatomic ion
惰性电子对
inert pair
二环的
bicyclic
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有机化学双语教学补充材料
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二硫化物
disulfide
二氯甲烷
dichloromethane(CH2Cl2)
二元化合物
binary compound
反错构象
Anti clinal
反芳香性的
anti-aromatic
反键轨道
antibonding orbital
反平面
Anti periplanar
反式
Trans
反式的
Anti
反式构象
anti conformation
反式加成
Anti addition
范德华力
van der Waals’ radius
芳环; 芳族环
aromatic ring(Ar)
芳基
aryl group
芳烃
aromatic hydrocarbon
芳香烃
arene
芳族化合物; 芳香族化合物
aromatic compound
非苯芳烃
nonbenzenoid aromatic hydrocarbon
非等时同步
Anisochronous
非对映异构的
Diastereotopic
非对映异构体
Diastereoisomers
非手性、非手性的
Achiral
肥皂
soap
费歇尔投影式
Fischer projection
分馏
fractional distillation
分歧、不同
allo-
分子单元
formula unit
分子轨道理论
molecular orbital theory
分子几何; 分子几何结构
molecular geometry
分子离子
molecular ion
分子量
molecular weight
分子模型
molecular model
分子筛
molecular sieve
分子式
molecular formula
酚
phenol
酚酸
phenolic acid
酚酞
phenolphthalein
风化的
efflorescent
砜
sulfone
干馏
dry distillation
甘油
glycerol
甘油, 丙三醇
glycerol(HOCH2CH(OH)CH2OH)
甘油三酸酯
triglyceride
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理学院应用化学系有机化学教研室
高分子化合物
polymer
隔离双键
isolated double bonds
共扼二烯烃
conjugated diene
共轭碱
conjugate base
共轭双键
conjugated double bonds
共轭酸
conjugate acid
共价键
covalent bond
共振结构
resonance structures
共振结构式
Canonical forms
共振效应
resonance effect
构象
conformation
构象异构体
conformers
构型
Configuration
构造异构体
constitutional isomers
固体石蜡
paraffin wax
官能团
functional group
冠醚
crown ether
光学纯
Enantiomerically pure (optically pure)
光学纯的
Optically pure
轨道
orbital
国际纯粹与应用化学联合会
IUPAC
过渡态
transition state
过氧化物离子
superoxide ion
合成材料
synthetic material
合成纤维
synthetic fiber
合成橡胶
synthetic rubber
核磁共振
NMR
核间距离， 键长
bond length
核酸外切酶
Exo
红外光谱
IR spectroscopy，infrared spectroscopy
胡萝卜素
carotene
互变体; 互变异构体
tautomer
互变异构现象
tautomerism
化学计量学; 化学计量法
stoichiometry
化学键
chemical bond
化学式量; 分子量
formula weight
化学位移
chemical shift
环化加成反应
Cycloaddition reaction
环氧化合物
epoxide
缓冲溶液
bufferpH buffer; buffer solution.
磺化反应
sulfonation reaction
磺基
sulpho group
磺酸
sulfonic acid
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有机化学双语教学补充材料
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混酸甘油酯
mixed glyceride
活性亚甲基
active methylene group
基（后缀）
-yl
极性分子
polar molecule
极性键
polar bond
几何异构体
geometric isomer
加成反应
addition reaction
加成化合物
addition compound
加聚反应
addition polymerization
甲基
methyl(-CH3)
甲烷
methane
价电子
valence electron
价键
valence bond
假旋转
Pseudorotation
间位定位
meta-directing
碱; 基极
base
碱的、碱性的
alkaline
碱水解常数
base hydrolysis constant
碱土金属
alkaline earth
键焓
bond enthalpy
键级
bond order
键能
bond energy
交叉式构象
Conformation (staggered)
交叉式构象
staggered conformation
结构式
structural formula
腈
nitrile
肼、联氨
hydrazine(NH2NH2)
锯架投影式
Sawhorse projection
聚合反应
po1ymerization
均裂
Homolytic bond cleavage
卡宾、碳烯
Carbene R2C:.
醌
quinone
蜡
wax
离去基团
Leaving group
离子电离; 离子电离作用
ionic dissociationionize; ionization.
离子盐
ionic compound salt
立体化学
stereochemistry
立体特异性的，立体专一性的
Stereospecific
立体选择性的，立体有择性的
Stereoselective
立体异构体
Stereoisomers
两性的
amphoteric
两性离子
zwitterion
两性溶剂
amphiprotic solvent
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理学院应用化学系有机化学教研室
裂化
cracking
裂解
pyrolysis
邻
Orthogonal
邻近的
Vicinal
硫醇
thiol
硫酚
thiophenol
硫化物
sulfide
卤代烃
halohydrocarbon
卤离子
halide ion
路易斯碱
Lewis base
路易斯结构
Lewis structure
路易斯酸
Lewis acid
螺环化合物
spiro compound
螺旋度; 螺旋性
Helicity
马尔科夫尼科夫规则
Markovniknov’s rule
麦芽糖
maltose
煤
coal
酶
enzyme
醚
ether
命名法; 命名原则
nomenclature
内
Endo
内酰胺
lactam
内消旋化合物
meso compounds
内酯
lactone
扭曲式构象
Conformation (skewed)
扭转位阻
Torsion barrier
纽曼投影式
Newman projection
偶氮
azo
偶极矩
dipole moment
配体; 配基
ligand
配位数
coordination number
平键; 平伏键
Equatorial bond
平均键焓
average bond enthalpy
平面偏振光
Plane polarized light
葡萄糖
glucose
前手性
Prochiral
强酸
strong acid
羟基
hydroxy group
羟基酸
hydroxy acid
桥环化合物
bridged ring compound
桥头碳原子
Bridgehead carbon
亲电体; 亲电子试剂
Electrophile
亲核试剂
Nucleophile
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有机化学双语教学补充材料
王俊儒等编
亲核性
nucleophilicity
亲双烯体
dienophile
氢键
hydrogen bond
氢氧化物
hydroxide
氢氧化物、水合物
hydrate
氰基
cyano group
巯基
mercapto
巯基
sulfhydryl group
区域选择性
Regioselective
取代反应
substitution reaction
取代基
substituent
取代酸
substituted acid
全规的；全同立构的
Isotactic
醛
aldehyde(RCHO)
醛的后缀
-al
炔烃
alkyne
热力学
thermodynamics
热力学产物
thermodynamic product
弱酸
weak acid
叁键
triple bond
石蜡
paraffin
石蕊试纸
litmus paper
石油
Petroleum
实验式; 经验式;
empirical formula
手性; 手性的
chiral
手性分子
chiral molecule
手性中心
chiral center
手性中心、不对称中心
Stereogenic centre (Chiral centre, Asymmetric centre)
双分子亲核取代反应
SN2 reaction
双分子消除反应
E2 elimination reaction
双峰; 双重谱线
doublet
双键
double bond
双烯; 二烯烃
diene
双原子分子
diatomic molecule
水合氢离子
hydronium ion(H3O+)
水解反应
hydrolysis reaction
水煤气,蓝煤气；合成气
water gas;blue gas; synthesis gas
顺错构象
Syn clinal
顺式
Cis
顺式；同；共；
Syn
顺式共平面
Syn periplanar
顺式加成
syn addition
顺旋
Conrotatory
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理学院应用化学系有机化学教研室
赤式
Erythro
塑料
plastic
塑料的老化
plastic ageing
酸、酸的
acid
酸电离常数
acid dissociation constant.
酸酐
acid anhydride
酸碱指示剂
acid-base indicator
羧基
carboxyl group
羧酸
carboxylic acid
缩氨脲
semicarbazone
缩酮
ketal
碳水化合物、糖类
carbohydrate
碳正离子
carbocation
羰基
carbonyl group
糖
sugar
天然产物
natural product
铁离子
ferric ion.
烃、碳氢化合物
hydrocarbon
烃的衍生物
derivative of hydrocarbon
烃基
hydrocarbonyl
同侧的
Suprafacial
同分异构体
isomer
同系物
homo1og
同系物; 同系化合物
homolog
铜离子
cupric. (Cu2+) cupric ion
酮
ketone
酮
ketone(R-CO-R')
酮酸
keto acid
脱氢酶
Dehydrogenases
歪扭构象; 偏转构象
Gauche conformation
外消旋化作用
Racemization
外消旋混合物
racemic mixture
烷基
alkyl group
烷基
alkyl(-CnH2n+1) alkyl group.
烷烃
alkane paraffin.
烷氧基
alkoxyl group
王水
aqua regia
未共用电子对
lone pair
位阻
steric hindrance
位阻异构体
Atropisomers
肟
oxime
无机化合物
inorganic compound
无机化学
inorganic chemistry
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有机化学双语教学补充材料
王俊儒等编
无水的
anhydrous
西佛碱
shiff's base
吸湿的
Hygroscopic
吸湿性; 吸水性
hygroscopicity
烯丙基
allyl group
烯丙基正离子
allylic carbon
烯烃
alkene
洗涤剂
detergent
洗脱; 洗脱法；洗剂
Elution
纤维素
cellulose
酰胺
amide
酰基
acyl group
酰卤
acid halide
消去反应
elimination reaction
消旋体
Racemate
硝化反应
nitratlon reaction
硝基
nitro group
硝酸，王水
nitric acid. (HNO3) aqua fortis
协定的, 一致的；协同的
Concerted
偕的
Geminal
辛烷
octane
休克尔规则
Hückel's rule
溴的四氯化碳溶液
solution of bromine in carbon tetrachloride
溴水
bromine water
旋光计
Polarimeter
旋光性
optical activity
亚氨基
imino group
亚砜
sulfoxide
亚磺酸
sulfinic acid
亚铁离子
ferrous ion
亚铜离子
cuprous. (Cu+) cuprous ion
亚硝基
nitroso group
盐析
salting-out
阳离子
cation
乙醇
ethanol
乙二胺四乙酸
EDTA
乙醛
ethana1
乙炔
ethyne
乙酸
acetic acid
乙酸
ethanoic acid
乙酸乙酯
ethyl acetate
乙缩醛二乙醇
acetal
乙烯
ethene
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理学院应用化学系有机化学教研室
乙酰乙酸乙酯
ethyl acetoacetate
椅式构象
Conformation (chair)
椅型构象; 椅式构象
Chair conformation
异头物
Anomers
异位的
Syndiotactic
阴离子
anion
阴碳离子; 负碳离子
carbanion
银镜反应
silver mirror reaction
硬脂酸、十八酸
stearic acid
油脂
oils and fats
有机化合物
organic compound
有旋光活性的
optically active
右旋的
Dextrorotatory (d)
诱导效应
inductive effect
原子化热
enthalpy of atomization. ( Hat)
杂化; 杂交
Hybridization
杂化轨道
hybrid orbitals
杂环的, 不同环式的
heterocyclic
皂化作用
saponification
蔗糖
sucrose
正交
ortho
脂肪酸
fatty acid
脂肪族的
aliphatic
脂环烃
alicyclic hydrocarbon
直角的；正交的
ortho-para director
直立键
Axial bonds
指纹区
fingerprint region
酯
ester
酯化反应
esterification
质谱法
mass spectrometry
质子
proton
质子给体; 质子给予体
proton donor
质子溶剂
protic solvent
中和反应
neutralization reaction
中间体
intermediate
中介效应
mesomeric effect
中性的
neutral
重氮化; 重氮化作用
diazotization
重氮盐
diazonium salt
重叠式构象
Conformation (eclipsed)
重叠式构象
轴手性；轴不对称性
重键;
多重键
自由基，根，原子团
eclipsed
conformation
Axial chirality
multiple
radical bond
周环反应
自由基; 游离基
Pericycl
ic reactions
free radical
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有机化学双语教学补充材料
腙
hydrozone
左旋的
Laevorotatory (l)
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王俊儒等编