Chapter 15 Functional Derivatives of Carboxylic Acids
Multiple Choice
1. Which is the correct structure for phenyl benzoate? (Sec. 15.2)
O
O
CO
a)
b)
OCCH2
O
O
c)
CH2OCCH2
d)
CH2OC
2. Which compounds are named correctly? (Sec. 15.2)
O
O
O
O
O
O
CH3CH2COCH3
succinic anhydride
I
O
O
O
-butyrolactone
IV
a)
b)
c)
d)
ethyl acetate
III
cyclohexyl anhydride
II
HCN
CH3
CH3
N,N-dimethylformamide
V
I, II, III
II, III, IV
I, IV, V
III, IV, V
3. Which is the common name for the following compound? (Sec. 15.2)
O
CNH2
OH
a)
b)
c)
d)
aspirin
cyclosporin
succinamide
salicylamide
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Chapter 15 Functional Derivatives of Carboxylic Acids
4. Which functional groups are correctly named? (Sec. 15.2)
O
O
O
HCN
CH3
O
CH3CH2COCH3
CH3
anhydride
I
amide
II
ester
III
O O
O
CH3CH2COCCH2CH3
acyl chloride
V
lactone
IV
a)
b)
c)
d)
CH3CCl
II, III, IV
III, IV, V
II, III, V
I, II, IV
5. What is the order of decreasing reactivity toward nucleophilic acyl substitution for these carboxylic acid
derivatives (most reactive first)? (Sec. 15.3)
O
O
O
O O
CH3COCH3
CH3CCl
CH3CNH2
CH3COCCH3
I
II
III
IV
a)
b)
c)
d)
II, IV, I, III
III, IV, I, II
IV, I, II, III
I, II, III, IV
6. Carboxylic acids and amides have in general higher boiling points than esters and anhydrides because of
which property? (Sec. 15.2, 14.4)
a)
b)
c)
d)
dispersion forces
resonance stabilization
conjugated functional groups
hydrogen bonding
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Chapter 15 Functional Derivatives of Carboxylic Acids
7. Which is the order of increasing boiling point of the following compounds (lowest first)?
(Sec. 15.2, 14.4)
O
O
CH3COCH3
I
a)
b)
c)
d)
CH3CCl
II
O
O
CH3CNH2
III
CH3COH
IV
IV, I, III, II
I, III, IV, II
II, I, III, IV
IV, III, II, I
8. Which is the order of increasing solubility in water of the following compounds (least first)?
(Sec. 15.2, 14.4)
O
O
CH3CH2COCH3
CH3CH2CCl
I
II
O
O
CH3CH2CNH2
CH3CH2COH
IV
III
a)
b)
c)
d)
I, III, II, IV
III, I, IV, II
I, IV, II, III
II, I, III, IV
9. Which reactions proceed at room temperature as written? (Sec. 15.4, 15.6, 15.7)
O
O
I CH3CH2CCl + H2O
O
CH3CH2COH + HCl
O
II CH3CH2CNH2 + H2O
O O
CH3CH2COH + NH3
III CH3COCCH3 +2 NH3
CH3CNH2 + CH3CO NH4
O
O
O
IV HCOCH2CH3 + NH3
a)
b)
c)
d)
O
HCNH2 + CH3CH2OH
I, II
I, III
II, III
II, IV
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Chapter 15 Functional Derivatives of Carboxylic Acids
10. The following reaction is fastest when Z is which group? (Sec. 15.3)
O
O
C
Z + OH
CO
+ HZ
O
O
CH3
a)
CH3O
b)
CH3CO
c)
d)
11. Which is the major product when 1,2-diaminoethane is heated with dimethyl oxalate? (Sec. 15.6)
O
O
O
b) O
O
O
a) CH3CN CH2CH2 NCCH3
H
H
O
O
O
c) HN
NH
H
d) CH3CN C
O
NCCH3
H CH3 H
12. Which are the best conditions for the following preparation? (Sec. 15.6)
O
O
COH
CN
CH3
CH3
CH3
CH3
a)
b)
c)
d)
SOCl2
NaOH
NH3
(CH3)2NH
(CH3)2NH
CH3CH2Br
(CH3)2NH
room temp
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Chapter 15 Functional Derivatives of Carboxylic Acids
13. Which compounds will yield benzoic acid when hydrolyzed? (Sec. 15.4)
I) benzyl ethanoate
II) benzamide
III) phenyl ethanoate
IV) methyl benzoate
a)
b)
c)
d)
I, II
III, IV
I, III
II, IV
14. Which is the product from the following reaction? (Sec. 15.6, 15.9)
O
NH3
1) LiAlH4
O
2) H2O
H
H
N
CH2CH2OH
N
a)
b)
OH
c)
OH
d)
CH2CH2NH2
NH2
15. Which of the following compounds does not yield nicotinamide when reacted with ammonia at room
temperature? (Sec. 15.6)
O
O
OH
Cl
N
N
I
a)
b)
c)
d)
O
O
O
N
I, II
II, IV
II, III
III, IV
180
CH3
OCH3
N
III
II
O
IV
Chapter 15 Functional Derivatives of Carboxylic Acids
16. Which is the product of the reaction of 4-aminophenol with 1 equivalent of acetic anhydride?
(Sec. 15.5)
O
NH2
O
HNCCH3
NH2
O
HNCCH3
CCH3
a)
b)
OCCH3
c)
d)
OH
OH
OCCH3
O
O
17. Which is the product of the reaction of phthalic anhydride with 1 equivalent of methanol? (Sec. 15.5)
O
O
O
O O
COH
COCH3
CCH3
COCCH3
a)
b)
c)
d)
COCH3
COCH3
COH
COH
O
O
O
O
18. Which reactions can be used to prepare an ester? (Sec. 15.5)
OH
O
SOCl2
COH
I
O
OH
CO Na
II
+
O
COH
III
OH
+
O
IV
a)
b)
c)
d)
OH
CNH2 +
II, IV
I, III
I, II
III, IV
181
H3O
heat
Chapter 15 Functional Derivatives of Carboxylic Acids
19. Which is the final product of a series of reactions starting with ethyl benzoate and reacting with
1) aqueous sulfuric acid and heat, 2) thionyl chloride, and 3) ethylamine? (Sec. 15.4, 15.6)
O
a)
NCH2CH3
b)
CNCH2CH3
H
H
O
c)
NCCH3
OH
d)
CHNCH2CH3
H
H
20. Which is the product from the reaction of sodium benzoate and acetyl chloride? (Sec. 15.5, 15.6)
O
a)
c)
O
COCH3 b)
OCCH3
O
O O
CCH3 d)
COCCH3
182
Chapter 15 Functional Derivatives of Carboxylic Acids
21. Partial hydrolysis of phenobarbitol gives which compound? (Sec. 15.4)
O
NH
C6H5
O
CH3CH2
NH
O
O
COH O
O
I
H2NCNH2
II
C
COH
CH2CH3
O
OO
COH
III H2NCCOH
IV
CNH2
CH2CH3
a)
b)
c)
d)
I, II
II, III
III, IV
I, III
22. Which is the product of the reaction of ethyl benzoate with 2 equivalents of methyl grignard followed
by aqueous acid? (Sec. 15.8)
a)
O
CH3
O
CCH3
COH
COCH3
b)
CH3
c)
183
CH2CH2CH3
d)
Chapter 15 Functional Derivatives of Carboxylic Acids
23. Which is the major product of the following reaction? (Sec. 15.8)
O
O
1)
CH3CH2MgBr
2)
H3O
+
HO
a)
OH
b)
CH3CH2
CH2CH3
HO
CH3CH2
OH
CH2CH3
d)
c)
O
CH3
CH3CH2
CH2CH3
OH
CH2CH3
24. Which are the best conditions for the following reaction? (Sec. 15.9)
O
CH3CH2CH2COCH2CH3
a)
1) NaBH4 / ether
2) H2O
b)
1) LiAlH4 / ether
2) H2O
c)
d)
CH3CH2CH2CH2OH
1) CH3CH2MgBr / ether
2) H3O
+
1) NH3
2) H3O+
184
Chapter 15 Functional Derivatives of Carboxylic Acids
25. Which are the best conditions for the following reaction? (Sec. 15.9)
O
O
CH3CCH2COCH2CH3
a)
1) NaBH4 / ether
2) H2O
b)
1) LiAlH4 / ether
2) H2O
c)
d)
OH
O
CH3CHCH2COCH2CH3
1) CH3CH2MgBr / ether
2) H3O
+
1) NH3
2) H3O+
Fill in the Blank
1. The IUPAC name of the following compound is ______________________________. (Sec. 15.2)
O
O
2. The IUPAC name of the following compound is ______________________________. (Sec. 15.2)
O
N
3. The reagents that complete the following reaction are,
O
O
OH
O
(Sec. 15.4)
185
Chapter 15 Functional Derivatives of Carboxylic Acids
4. The starting material that completes the following reaction is,
O
HN
N
(Sec. 15.6)
5. The reagents that complete the following reaction are,
O
O
Cl
O
(Sec. 15.5)
6. The major product that completes the following reaction is,
MgBr
O
1)
O
2) H+, H2O
(Sec. 15.8)
7. The reagents that complete the following reaction are,
O
N
N
(Sec. 15.9)
8. The reagents that complete the following reaction are,
O
O
N
H
OH
186
(Sec. 15.4)
Chapter 15 Functional Derivatives of Carboxylic Acids
9. The major product that completes the following reaction is,
OH
Cl
O
(Sec. 15.5)
10. The major product that completes the following reaction is,
O
O
H2O
O
(Sec. 15.4)
True-False
1. The order of reactivity of the carboxylic acid derivatives with water is,
O
O
O
>
O
O
>
Cl
O
OCH2CH3
>
NH2
(Sec. 15.3)
2. The order of reactivity of the carboxylic acid derivatives with ammonia is,
O
O
>
>
NH2
OCH2CH3
O
O
O
>
O
Cl (Sec. 15.3)
3. The name of the following compound is 3-methylbutanoyl 2-methylbutanoate. (Sec. 15.2)
O
O
O
187
Chapter 15 Functional Derivatives of Carboxylic Acids
4. The structure for cyclohexanecarboxylic 2,2-dimethylpropanoic anhydride is,
O
O
O
(Sec. 15.2)
5. The product of the reaction of 5-pentanolactam with aqueous acid and heat is 5-aminopentanoic acid.
(Sec. 15.4)
6. The product of the reaction of 4-butanolactone with ethanol and acid is butanoic acid and diethylether.
(Sec. 15.5)
7. The product of the reaction of propanamide with ethanol is ethyl propanoate. (Sec. 15.5)
8. Sodium borohydride reduces propanamide to propanamine. (Sec. 15.9)
9. Lithium aluminum hydride reduces 3-oxobutanoic acid to 4-hydroxy-2-butanone. (Sec. 15.9)
10. The proper mechanism for the reaction of acetyl chloride and water is shown below. (Sec. 15.3)
O
O
Cl
O
Cl
O
H + H
Cl
OH
H2O
188
O
+ ClOH
Chapter 15 Functional Derivatives of Carboxylic Acids
Answers
Multiple Choice
1. a
2. c
3. d
4. c
5. a
6. d
7. c
8. d
9. b
10. d
11. c
12. a
13. d
14. d
15. b
16. b
17. a
18. b
19. b
20. d
21. a
22. b
23. a
24. b
25. a
Fill in the Blank
1.
2.
3.
4.
E – 1-methylethyl 2-pentenoate or E – isopropyl 2-pentenoate
N,N-dimethyl cyclohexane carboxamide
H2O, H+
As written,
O
O
O
Cl
or
O
if heat is assumed,
O
OR
may also be correct
189
Chapter 15 Functional Derivatives of Carboxylic Acids
5.
HO
6.
OH
7. 1) LiAlH4, ether 2) H2O
8. H2O, H+, heat
9.
O
O
10.
O
OH
2
True-False
1. T
2. F
3. F
4. T
5. T
6. F
7. F
8. F
9. F
10. T
190