TKJ4102: Selvstendig prøve 2 / 2010
What is the relationship between the following two compounds?
H CH3
H3C H
1.
and
CH3
A)
B)
C)
D)
CH3
identical
enantiomers
diastereomers
constitutional isomers
2. Which of the following amines gives a pair of diastereomeric salts when reacted
with (S)-(-)-malic acid?
O
O
HOCCH2CHCOH
(malic acid)
OH
CH3CHNH2
(CH3)2CNH2
C6H5
A)
B)
C)
D)
E)
A
only A
only B
only C
A and C
A, B, and C
CH3CHCH2NH2
C6H5
C6H5
B
C
3. Which of the following is a diastereomer of (2R,3R)-2,3-dibromopentane?
A)
B)
C)
D)
(2S,3S)-2,3-dibromopentane
(2S,3R)-2,3-dibromopentane
R-1,2-dibromopentane
(2R,4R)-2,4-dibromopentane
4. Which compound below has a meso form?
A)
B)
C)
D)
1,2-dichlorobutane
1,3-dichlorobutane
2,3-dichlorobutane
1,4-dichlorobutane
Page 1
5. Which of the following is the enantiomer of (2R,3R)-2,3-dibromopentane?
A)
B)
C)
D)
(2S,3S)-2,3-dibromopentane
(2S,3R)-2,3-dibromopentane
(2R,3S)-2,3-dibromopentane
(2R,4R)-2,4-dibromopentane
6. The rate law for the following reaction is:
DMSO
CH3CH2CH2Cl + NaCN
A)
B)
C)
D)
rate = k[CH3CH2CH2Cl]
rate = k[CH3CH2CH2Cl][NaCN]
rate = k[CH3CH2CH2Cl][NaCN]2
rate = k[CH3CH2CH2Cl]2[NaCN]
7. Give the product(s) of the following reaction?
CH2Br
NaSH
Br
CH2Br
1)
2)
SH
A)
B)
C)
D)
CH2SH
CH2SH
3)
Br
4) a mixture of 1 and 2
SH
is 1
is 2
is 3
is 2
8. Which of the following does not correctly describe SN2 reactions of alkyl halides?
A) Tertiary halides react faster than secondary halides.
B) Rate of reaction depends on the concentrations of both the alkyl halide and the
nucleophile.
C) Inversion of configuration occurs at the carbon atom bonded to the halide.
D) The transition state species has a pentavalent carbon atom.
Page 2
9. Which of the following is the rate law for the SN1 mechanism of an alkyl halide with
a nucleophile?
A)
B)
C)
D)
rate = k[alkyl halide]
rate = k[nucleophile]
rate = k[alkyl halide][nucleophile]
rate = k[alkyl halide]2[nucleophile]
10. Starting with toluene, which of the following is the best synthesis of
meta-bromobenzoic acid?
1) (1) Br2, FeBr3
(2) K2Cr2O7, H2SO4 (heat)
A)
B)
C)
D)
2) (1) Br2, hv
(2) K2Cr2O7, H2SO4 (heat)
3) (1) K2Cr2O7, H2SO4 (heat)
(2) Br2, FeBr3
4) (1) K2Cr2O7, H2SO4 (heat)
is 1
is 2
is 3
is 4
(2) Br2, hv
11. Rank the following anions in order of increasing base strength.
A)
B)
C)
D)
A. CH3CH2
A<B<C
B<C<A
C<B<A
C<A<B
B. H2C CH
C. HC C
12. When a terminal alkyne is treated with sodium amide in liquid ammonia, sodium
amide acts as a:
A)
B)
C)
D)
Bronsted acid
Bronsted base
reducing agent
catalyst
13. Which of the following describes the C(2) - C(3) sigma bond in the structure below?
HC C C CH
A)
B)
C)
D)
sp-sp
sp2-sp2
sp3-sp3
2p-2p
Page 3
14. Which of the following is the correct IUPAC name of the product for the reaction
shown below?
Na, NH3
CH3C CCH2CH2CH(CH3)2
A) cis-2-methyl-5-heptene
B) trans-2-methyl-5-heptene
C) cis-6-methyl-2-heptene
D) trans-6-methyl-2-heptene
15. Which one of the following gives only a single allylic bromide on heating with NBS
in carbon tetrachloride?
1)
A)
B)
C)
D)
2)
3)
4)
is 1
is 2
is 3
is 4
16. Which of the following is the 1,4-addition product in the reaction shown below?
HBr
Br
1)
Br
3)
Br
2)
4)
Br
A)
B)
C)
D)
is 1
is 2
is 3
is 4
17. Which one of the following is not true concerning Diels-Alder reactions?
A)
B)
C)
D)
The reaction is stereospecific.
The reaction mechanism has only one step.
The reaction mechanism involves a resonance stabilized carbocation.
The diene must be a conjugated diene.
Page 4
18. Give the total number of resonance forms of the carbocation which results from the
SN1 ionization of the compound shown below.
Br
A)
B)
C)
D)
E)
no resonance forms - a single Lewis structure
two
three
four
six
19. What is the relationship between the structures shown below?
and
A)
B)
C)
D)
constitutional isomers
different conformations of the same compound
diastereomers
resonance forms
20. Which of the following isomers would you predict has the highest heat of
hydrogenation?
A)
B)
C)
D)
1-ethyl-1,4-cyclohexadiene
3-ethyl-1,4-cyclohexadiene
1-ethyl-1,3-cyclohexadiene
5-ethyl-1,3-cyclohexadiene
21. Which one of the following is not a resonance form of the benzyl free radical?
CH2
1)
A)
B)
C)
D)
CH2
2)
CH2
3)
is 1
is 2
is 3
is 4
Page 5
CH2
4)
22. How many isomeric tribromobenzenes are possible?
A)
B)
C)
D)
E)
one
two
three
four
five
23. Which of the following is an aromatic hydrocarbon?
1)
A)
B)
C)
D)
2)
3)
4)
is 1
is 2
is 3
is 4
24. Identify the aromatic compounds.
A)
B)
C)
D)
N
H
N
A
B
C
A and B
C and D
A, B, and D
all of them
Page 6
D
25. Starting with toluene, which sequence of reactions below work best to prepare the
following cyclohexadiene compound.
CH2OCH3
1) toluene
Na, NH3
CH3OH
NBS, heat
CCl4
NaOCH3
CH3OH
2) toluene
NBS, heat
CCl4
NaOCH3
CH3OH
Na, NH3
CH3OH
NaOCH3
Na, NH3
NBS, heat
CH3OH
CH3OH
3) toluene
CCl4
4) all the above would be good syntheses
A)
B)
C)
D)
is 1
is 2
is 3
is 4
26. What is the product of the following series of reactions?
O
HNO3
Br2
Zn(Hg)
C
H2SO4
FeBr3
HCl
O2N
1)
CH2
3)
NO2
CH2
Br
Br
O2N
2)
A)
B)
C)
D)
Br
is 1
is 2
is 3
is 4
4)
CH2
NO2
Page 7
CH2
Br
27. What is the electrophile in the Friedel-Crafts alkylation reaction below?
C(CH3)3
(CH3)3CCl
AlCl3
A)
B)
C)
D)
AlCl3
Clbenzene
(CH3)3C+
28. Arrange the following compounds in order of increasing reaction rate with
HNO3/H2SO4?
(A) C6H5CH=O
(B) C6H5OCH3
(C) C6H5Br
(D) C6H5CH3
A)
B)
C)
D)
A<C<D<B
A<D<C<B
C<A<B<C
C<A<D<B
Page 8
29. Starting with toluene, which of the following is the best method to make the ether
shown
below? (assume you can separate ortho and para isomers)
Cl
A)
B)
C)
D)
CH2 O
is 1
is 2
is 3
is 4
30. The reaction of 3-methylcyclohexanone with CH3MgBr followed by neutralization
gives two alcohols. These two alcohols are;
A)
B)
C)
D)
constitutional isomers
enantiomers formed in equal amounts
enantiomers formed in unequal amounts
diastereomers
Page 9
31. Which of the following are intermediates in the reaction below?
H3C
CH3
C C
H
+ CHCl3
H3C
KOC(CH3)3
Cl
H
H
CH3
H
Cl
A)
B)
C)
D)
1) CHCl2 and CCl2
3) HCCl2 and
2) CCl3 and
4) CCl3
CCl2
and
CCl2
CCl2
is 1
is 2
is 3
is 4
32. What is the product of the reaction shown below?
CH3CH2CH2CH2Br
A)
B)
C)
D)
Li, 0oC
CuI, -20oC
diethyl ether
CH3(CH2)3CH2Br
THF
4-nonene
nonane
4-bromononane
5-bromononane
33. Which of the following are intermediates in the reaction of excess methylmagnesium
bromide with ethyl benzoate (shown below) to make 2-phenyl-2-propanol?
O
C6H5COEt + CH3MgBr (xs)
OMgBr
C6H5
C OCH2CH3
diethyl ether
C6H5
A)
B)
C)
D)
OMgBr
O
C CH3
CH3
A
H3O+
C6H5
C CH3
CH3
B
A and B
A and C
B and C
A, B, and C
Page 10
C
34. Select the strongest base in the following.
1) NaNH2
A)
B)
C)
D)
2) CH3Li
3) NaOCH2CH3
4) HC CNa
is 1
is 2
is 3
is 4
35. The alcohol product(s) of the reduction of 2-methyl-3-pentanone with LiAlH4 is
(are):
O
1) LiAlH4, diethyl ether
2) H2O
A)
B)
C)
D)
a single enantiomer.
a racemic mixture.
two diastereomers.
two constitutional isomers.
36. What is the product of the reaction below?
O
CH3COH +
CH3CH2CH2OH
H2SO4
heat
O
1) CH3CH2COCCH3
O
2) CH3COCH2CH2CH3
A)
B)
C)
D)
O
3) CH3CH2CH2CCH3
O
4) CH3CH2COCH2CH3
is 1
is 2
is 3
is 4
37. Which of the following cannot be made by the reduction of a ketone or aldehyde
with NaBH4 in methanol?
A) 1-butanol
B) 2-butanol
C) 2-methyl-1-propanol
D) 2-methyl-2-propanol
Page 11
38. Which compound below is the product expected from the following reaction?
O
H3C
O CCH3
O
1) LiAlH4, diethyl ether
2) H2O
H
O
H3C
O CCH3
OH
1)
HO
OH
3)
CH3
OH
H3C
OH
2)
H3C
CH2OH
H
4)
O
A)
B)
C)
D)
is 1
is 2
is 3
is 4
39. What is the product of the following reaction?
O
(1) LiAlH4
(2) H2O
OH
O
1)
3)
OH
OH
2)
4)
OH
A)
B)
C)
D)
is 1
is 2
is 3
is 4
Page 12
40. Which one of the following reaction steps work best to carryout the transformation
shown below?
?
1)
1) BH3, THF
2) H2O2, NaOH
2)
H2O, H2SO4 (cat.)
?
H
PCC
3)
CH2Cl2
O
1) BH3, THF
HIO4
2) H2O2, NaOH
PCC
4)
OsO4
(CH3)3COOH
K2Cr2O7, H2SO4
H2O
-
OH
A)
B)
C)
D)
is 1
is 2
is 3
is 4
41. Which reagent(s) below converts cyclohexene to trans-1,2-cyclohexanediol?
1) OsO4, (CH3)3COOH, (CH3)3COH, NaOH
2) O3 followed by Zn/H2O
O
3) CH3COOH followed by NaOH/H2O
4) HIO4
A)
B)
C)
D)
is 1
is 2
is 3
is 4
Page 13
42. The reaction shown below can be described as an:
OH
H3C CH CH2Br
A)
B)
C)
D)
O
NaOH, H2O
H3C CH CH2
acid-base reaction followed by an intramolecular Williamson ether synthesis.
acid-base reaction followed by an intramolecular SN1 reaction.
E2 reaction followed by an addition reaction to a double bond.
SN2 reaction followed by an intramolecular Williamson ether synthesis.
43. What is the final product of the following sequence of reactions?
O
PBr3
(CH3)2CHOH
Mg
diethyl ether
1) (CH3)2CHOCH2CH2OH
1)
PCC
2) H3O+
CH2Cl2
3) (CH3)2CHCH2CHO
O
2) (CH3)2CHCCH3
A)
B)
C)
D)
4) (CH3)2CHCH2CO2H
is 1
is 2
is 3
is 4
44. What is(are) the product(s) of the following nucleophilic ring-opening reaction?
O-Na+
O
H3C
1)
H3O+
H
H
H
OCHCH2OH
3)
OCH2CHOH
CH3
CH3
OH
2)
OCCH3
4)
OH
CH3
A)
B)
C)
D)
OCHCH2OH
is 1
is 2
is 3
is 4
Page 14
45. What is the product of the following reaction?
HBr (xs)
O
Br
Br
1)
3)
O
OH
Br
2)
OH
4)
Br
A)
B)
C)
D)
Br
is 1
is 2
is 3
is 4
46. Identify the correct IUPAC name of the compound below?
O
H
A)
B)
C)
D)
4-benzyl-5-methylhexanal
5-isopropyl-5-phenylbutanal
2-methyl-3-phenylhexanal
5-methyl-4-phenylhexanal
47. Which of the following is the product of the reaction between acetone, CH3COCH3,
and methylamine, CH3NH2?
NCH3
OH
OCH3
ONH2
1) CH3CCH3
2) CH3C=CHNCH3
3) CH3CCH3
NH2
A)
B)
C)
D)
is 1
is 2
is 3
is 4
Page 15
4) CH3CCH3
CH3
48. Which one of the following is not an intermediate in the acid-catalyzed reaction of
benzaldehyde with 2 equivalents of methanol to give benzaldehyde dimethyl acetal?
H
OCH3
OH2
OCH3
H
OCH
3
HO C H
1)
A)
B)
C)
D)
HO C H
HO C
2)
3)
H
C
4)
is 1
is 2
is 3
is 4
49. Which one of the following works best as the reaction steps to carry out the
conversion below?
CH CH2
?
CH2 CHO
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
O
4) (1) CH3COOH
A)
B)
C)
D)
(2) NaOH, H2O
is 1
is 2
is 3
is 4
50. Which reagent below would be used to convert 2-pentyne to trans-2-pentene?
A)
B)
C)
D)
NaNH2, NH3
Na, NH3
H2, Lindlar Pd
H2O, HgSO4/H2SO4
Page 16