Chapter 15 Functional Derivatives of Carboxylic Acids
Multiple Choice
1. Which is the correct structure for phenyl benzoate? (Sec. 15.2)
2. Which compounds are named correctly? (Sec. 15.2)
a) I, II, III
b) II, III, IV
c) I, IV, V
d) III, IV, V
3. Which is the common name for the following compound? (Sec. 15.2)
a) aspirin
b) cyclosporin
c) succinamide
d) salicylamide
4. Which functional groups are correctly named? (Sec. 15.2)
a) II, III, IV
b) III, IV, V
c) II, III, V
d) 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)
a) II, IV, I, III
b) III, IV, I, II
c) IV, I, II, III
d) 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) dispersion forces
b) resonance stabilization
c) conjugated functional groups
d) hydrogen bonding
7. Which is the order of increasing boiling point of the following compounds (lowest first)?
(Sec. 15.2, 14.4)
a) IV, I, III, II
b) I, III, IV, II
c) II, I, III, IV
d) 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)
a) I, III, II, IV
b) III, I, IV, II
c) I, IV, II, III
d) II, I, III, IV
9. Which reactions proceed at room temperature as written? (Sec. 15.4, 15.6, 15.7)
a) I, II
b) I, III
c) II, III
d) II, IV
10. The following reaction is fastest when Z is which group? (Sec. 15.3)
11. Which is the major product when 1,2-diaminoethane is heated with dimethyl oxalate? (Sec. 15.6)
12. Which are the best conditions for the following preparation? (Sec. 15.6)
13. Which compounds will yield benzoic acid when hydrolyzed? (Sec. 15.4)
I) benzyl ethanoate
II) benzamide
III) phenyl ethanoate
IV) methyl benzoate
a) I, II
b) III, IV
c) I, III
d) II, IV
14. Which is the product from the following reaction? (Sec. 15.6, 15.9)
15. Which of the following compounds does not yield nicotinamide when reacted with ammonia at room temperature? (Sec. 15.6)
a) I, II
b) II, IV
c) II, III
d) III, IV
16. Which is the product of the reaction of 4-aminophenol with 1 equivalent of acetic anhydride?
(Sec. 15.5)
17. Which is the product of the reaction of phthalic anhydride with 1 equivalent of methanol? (Sec. 15.5)
18. Which reactions can be used to prepare an ester? (Sec. 15.5)
a) II, IV
b) I, III
c) I, II
d) III, IV
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)
20. Which is the product from the reaction of sodium benzoate and acetyl chloride? (Sec. 15.5, 15.6)
21. Partial hydrolysis of phenobarbitol gives which compound? (Sec. 15.4)
a) I, II
b) II, III
c) III, IV
d) 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)
23. Which is the major product of the following reaction? (Sec. 15.8)
24. Which are the best conditions for the following reaction? (Sec. 15.9)
25. Which are the best conditions for the following reaction? (Sec. 15.9)
Fill in the Blank
1. The IUPAC name of the following compound is ______. (Sec. 15.2)
2. The IUPAC name of the following compound is ______. (Sec. 15.2)
3. The reagents that complete the following reaction are,
(Sec. 15.4)
4. The starting material that completes the following reaction is,
(Sec. 15.6)
5. The reagents that complete the following reaction are,
(Sec. 15.5)
6. The major product that completes the following reaction is,
(Sec. 15.8)
7. The reagents that complete the following reaction are,
(Sec. 15.9)
8. The reagents that complete the following reaction are,
(Sec. 15.4)
9. The major product that completes the following reaction is,
(Sec. 15.5)
10. The major product that completes the following reaction is,
(Sec. 15.4)
True-False
1. The order of reactivity of the carboxylic acid derivatives with water is,
(Sec. 15.3)
2. The order of reactivity of the carboxylic acid derivatives with ammonia is,
(Sec. 15.3)
3. The name of the following compound is 3-methylbutanoyl 2-methylbutanoate. (Sec. 15.2)
4. The structure for cyclohexanecarboxylic 2,2-dimethylpropanoic anhydride is,
(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)
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. E – 1-methylethyl 2-pentenoate or E – isopropyl 2-pentenoate
2. N,N-dimethyl cyclohexane carboxamide
3. H2O, H+
4. As written,
if heat is assumed,
may also be correct
5.
6.
7. 1) LiAlH4, ether 2) H2O
8. H2O, H+, heat
9.
10.
True-False
1. T
2. F
3. F
4. T
5. T
6. F
7. F
8. F
9. F
10. T
1