Name:
Chem 22
Final exam
Spring ‘00
1. What product is formed when 2,2-dimethylcyclohexanol undergoes acidcatalyzed dehydration?
a)
b)
c)
d)
e)
1,1-dimethylcyclohexene
2,2-dimethylcyclohexene
1,3-dimethylcyclohexene
1,2-dimethylcyclohexene
3,3-dimethylcyclhexen
2. What compound is formed from the acid-catalyzed rea tion of 2,3-epoxybutane
with methanol?
a)
b)
c)
d)
e)
ethylene glycol
2-methoxy-3-butanol
2,3-butandiol
3-ethoxy-2-butanol
3-methoxy-2-butanol
3. Which of the following statements is true?
a) Thiols have a pka values of about 16, and they are stronger acids than
alcohols.
b) Thiols have a pka values of about 16, and they are weaker acids than
alcohols
c) Thiols have a pka values of about 10, and they are stronger acids than
alcohols
d) Thiols do not have a pka values.
e) Thiols have a pka values of about 10, and they are weaker acids than
alcohols
4. Which of the following is not a true statement?
a) In an organometallic compound, the carbon bonded to the metal is the
nucleophile.
b) An epoxide is more reactive than an ether.
c) In a Hofmann elimination, a proton is removed from the beta carbon that
is bonded to the greater number of hydrogens.
d) Thioethers are also called sufides
5. What do PBr3, PCl3, and SOCl2 have in common?
a) they convert alcohols into alkyl halides
b) a and c
c) they convert an alcohol into an intermediate that has a leaving group that
can be displaced by a halide ion.
d) They react with alcohols without forming an intermediate
e) They undergo an E2 reaction with an alcohol.
6. What kind of reactions do aromatic compounds such as benzene undergo?
a)
b)
c)
d)
e)
electrophilic aromatic substitution reactions
nucleophilic addition reactions
electrophilic aliphatic substitution reactions
electrophilic addition reactions
nucleophilic aromatic substitution reactions.
7. What is the major product formed from the reaction of benzene with isobutyl
chloride and AlCl3?
a)
b)
c)
d)
e)
2-methyl-1-phenylpropane
2-phenylbutane
isobutylbenzene
2-methyl-2-phenylpropane
1-phenylbutane
8. Which of the following is the most activating substituent for electrophilic
aromatic substitution?
a)
b)
c)
d)
e)
–N(CH3)3+
- NH2
–NO2
–CH2NHCH3
–NH-C-(=O)-CH3
9. Which sequence of reactions will convert benzene into 2-phenylethanol?
a)
b)
c)
d)
e)
(1) Br2/FeBr3 (2) Mg/Et2O (3)ethylene oxide (4) H+
(1) ethylene oxide (2) H+ (3) Br2/FeBr3 (4) Mg/Et2O
(1) Mg/Et2O (2) Br2/FeBr3 (3) propylene oxide (4) H+
(1) Br2 (2)Mg/Et2O (3) propylene oxide (4) H+
(1) Br2/FeBr3 (2) Mg/Et2O (3) propylene oxide (4) H+
10. Which of the following compounds is the most acidic? (the substituents are parasubstuents.)
a)
b)
c)
d)
e)
O2NCH2-C6H4-COOH
CH3-C6H4-COOH
O=CH-C6H4-COOH
O2N-C6H4-COOH
CH3-C6H4-COOH
11. Which of the following represents the correct order of relative reactivity in a
nucleophilic acy substitution reaction?
a)
b)
c)
d)
e)
acyl halides> esters> acid anhydrides> amides
acyl halides> acid anhydrides> esters> amides
acid anhydrides> acyl halides> esters> amides
amides> carboxylic acids> acid anydrides> acyl halides
esters> acid anhydrides> acyl halides> amides
12. Which of the follwing is not a true statement?
a) An acid anhydride reacts with an alcohol to form an ester and a carboxylic
acid.
b) An acyl halide reacts with water to form a carboxylic acid.
c) An acyl halide reacts with an amine to form an amide
d) An ester reacts with an amine to form an amide.
e) An amide reacts with an alcohol to fomr an ester.
13. Which of the followng reagents can be used to convert a carboxylic acid into an
acyl chloride?
a)
b)
c)
d)
e)
PCl3
a and c
SOCl2
SO2Cl
SOCl
14. Which of the following is the best leaving group?
a)
b)
c)
d)
e)
CH3COOHOClNH3
NH2-
15. What product is formed when formic acid reacts with methyl amine at room
temperature?
a) No reaction occurs
b)
CH3COO-NH4+
c) HC (=O)-NH2
d) HCOO-CH3NH3+
e) HC(=O)-N(CH3)2
16. Which of the following compounds is the least reactive towards nucleophilic
attack?
a)
b)
c)
d)
e)
acetone
diisopropyl ketone
methyl propyl ketone
formaldehyde
acetaldehyde
17. Carbonyl compounds can be reduced to alcohols using sodium borohydride
followed by addition of H+/H2O. Which statement best describes the
mechanism?
a) addition of a hydrogen radical, flowed by addtion of a second hydrogen
radical
b) addition of a proton, followed by addition of a hydride ion
c) addition of a hydride ion, followed by addition of water
d) addition of a hydride ion, folloed by addition of a proton
e) addtion of a hydride ion and a proton more or less at the same time
18. Which of the following describes “reductive amination?”
a) an aldehyde or a ketone + a tertiary amine + H2/zeolite
b) an aldehyde or a ketone + ammonia or a primary or a secondary amine +
H2/Raney Ni
c) an aldehyde or a ketone + ammonia or a primary or a secondary amine +
H2O/Raney Ni
d) an aldehyde or a ketone + ammonia or a primary or a secondary amine +
H2/zeolite
e) an aldehyde or a ketone + ammonia or a primary or a secondary amine +
H2/zeolite
19. Which of the following reaction will form an alkane
a)
b)
c)
d)
an aldehyde + a Griganard reagent
a ketone + NH2NH2/HO-/heat
an aldehyde + H+/H2O
an aldehyde + sodium borohydride followed by H+/H2O
20. What sequence of reactions will conver CH3-C(=O)-CH2CH=O to
CH3CH(OH)CH2CH=O?
a)
b)
c)
d)
e)
(1) H2/Pt (2) PCC
(1) KMnO4/HO- (2) H+/H2O
(1) HOCH2CH2OH/H+ (2) NaBH4 (3) H+/H2O
(1) NaBH4 (2) H+/ H2O
(1) LiAlH4 (2) H+/H2O
21. Which of the follwing reactions is neither an oxidation nor a reduction?
a) Reaction of an alkene with Ozone
b) Reaction af an alkene with a perocyacid
c) Reaction of an alkene with hydrogen gas in the presence of a metal
catalyst.
d) Reaction of an alkene with water
e) Reaction of an alkene with bromine
22. What product is obtained when cyclohexene reacts with a cold, basic solution of
potassium permangante?
a)
b)
c)
d)
23.
a cis diol with both OH groups in axial positions
a cis diol with both OH groups in equatorial positions
a trans diol with both OH groups in equatorial positions
a cis dil with one OH group in an axial position and the other in an
equatorial position.