Chapter 21 - Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
IUPAC Naming Instructions: Provide proper IUPAC names.
1. Name:
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2. Name:
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3. Name:
ANSWER:
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4. Name:
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POINTS: 1
5. Name:
ANSWER:
POINTS: 1
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Chapter 21 - Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
Drawing Instructions: Draw structures corresponding to each of the given names.
6. Draw: 2-propenamide
ANSWER:
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7. Draw: 3,4,5-trimethoxybenzoyl chloride
ANSWER:
POINTS: 1
8. Draw: acetic formic anhydride
ANSWER:
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9. Draw: N,N-dimethylformamide
ANSWER:
POINTS: 1
10. Draw: methyl cis-3-ethylcyclobutanecarboxylate
ANSWER:
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11. Draw: (E)-2,4-dimethyl-2-hexenoyl chloride
ANSWER:
POINTS: 1
12. What is the correct structure for phenylbenzoate?
a.
b.
c.
d.
ANSWER:
POINTS: 1
Exhibit 21-1
What is the order of decreasing reactivity towards nucleophilic acyl substitution for the carboxylic acid derivatives? (most
reactive first)
13.
a.
I, II, III, IV
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Chapter 21 - Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
b. I, III, IV, II
c. II, IV, III, I
d. II, I, III, IV
ANSWER:
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1
14.
a. I, III, II, IV
b. II, III, I, IV
c. III, II, I, IV
d. IV, I, III, II
ANSWER:
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16. Write the complete stepwise mechanism for the basic hydrolysis of acetamide, shown below. Show all electron flow
with arrows and draw all intermediate structures.
ANSWER:
POINTS: 1
Exhibit 21-3
Consider the reaction below to answer the following question(s):
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Chapter 21 - Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
19. Refer to Exhibit 21-3. Write the complete stepwise mechanism for this reaction. Show intermediate structures and all
electron flow with arrows.
ANSWER:
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20. Refer to Exhibit 21-3. This reaction is an example of:
a. an intermolecular nucleophilic acyl substitution reaction
b. an intramolecular nucleophilic acyl substitution reaction
c. an intermolecular SN2 reaction
d. an intramolecular SN2 reaction
ANSWER:
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21. Refer to Exhibit 21-3. The purpose of the base catalyst in this reaction is:
a. to polarize the carbonyl group to make it more electrophilic
b. to convert the ester to an intermediate carboxylic acid
c. to convert the alcohol group to an alkoxide anion, which is a better nucleophile
d. all of the above
ANSWER:
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22. Refer to Exhibit 21-3. The product of this reaction is:
a. a lactone
b. an anhydride
c. a lactam
d. an ether
ANSWER:
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23. Methyl butanoate has been isolated from pineapple oil and can be prepared by the Fischer esterification reaction
shown below. Write the complete stepwise mechanism for this reaction. Show all electron flow with arrows and include
all intermediate structures.
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Chapter 21 - Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
ANSWER:
POINTS: 1
24. Write the complete stepwise mechanism for the acid-catalyzed hydrolysis of the following amide to yield mandelic
acid. Show all electron flow with arrows and draw the structures of all intermediate species.
ANSWER:
POINTS: 1
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Chapter 21 - Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
25. The purpose of the acid catalyst in the hydrolysis of an amide is:
a. to enhance the nucleophilicity of the water molecule
b. to enhance the electrophilicity of the amide carbonyl carbon
c. to enhance the electrophilicity of the water molecule
d. to shift the equilibrium of the reaction
ANSWER:
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Exhibit 21-4
Consider the information below to answer the following question(s).
The reaction of a carboxylic acid with an alcohol in the presence of acid is termed Fischer esterification.
26. Refer to Exhibit 21-4. The nucleophile in this reaction is _____.
ANSWER:
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27. Refer to Exhibit 21-4. Compound C functions as _____ in this reaction.
a. a base scavenger
b. a solvent
c. a catalyst
d. a neutralizer
ANSWER:
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28. Refer to Exhibit 21-4. Fischer esterification is an example of:
a. nucleophilic acyl addition
b. nucleophilic acyl substitution
c. nucleophilic acyl elimination
d. nucleophilic acyl rearrangement
ANSWER:
POINTS: 1
29. Refer to Exhibit 21-4. Write the stepwise mechanism for the Fischer esterification reaction of benzoic acid and
methanol given above. Show all electron flow by using curved arrows, and include all intermediate structures.
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Chapter 21 - Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
ANSWER:
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Exhibit 21-5
Provide structure(s) for the starting material(s), reagent(s) or the major organic product(s) of each of the following
reactions or sequences of reactions. Show all relevant stereochemistry.
30.
ANSWER:
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31.
ANSWER:
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32.
ANSWER:
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Chapter 21 - Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
33.
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34.
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35.
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36.
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37.
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Chapter 21 - Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
38.
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39.
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40.
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41.
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42.
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Chapter 21 - Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
43.
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Exhibit 21-6
Choose the best reagent(s) from the list provided below for carrying out the following transformations. Place the letter
corresponding to the best choice in the blank to the left of the transformation.
a. (Ph)2CuLi, ether
b. NaBH4, ethanol
c. 1.
2.
d. 1.
2.
e. (CH3)2CuLi, ether
f.
CH3MgBr, ether
H3O+
LiAlH4, THF
H3O+
1. DIBAH, toluene
2. H3O+
g. 1. (Ph)2CHMgBr
2. H3O+
h. 1. 2 PhMgBr, ether
2. H3O+
45. _____
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46. _____
ANSWER:
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47. _____
ANSWER:
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Chapter 21 - Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
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48. _____
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49. _____
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Exhibit 21-7
Show how you would accomplish each of the following transformations. More than one step may be required. Show all
reagents and all intermediate structures.
50.
ANSWER:
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51.
ANSWER:
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Chapter 21 - Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
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52.
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53.
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54. Aklomide, 2-chloro-4-nitrobenzamide, is an ingredient in veterinary antibacterial preparations. Propose a synthesis of
aklomide starting with toluene. Show all reagents and all intermediate structures.
ANSWER:
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Chapter 21 - Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
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55. Ethyl phenylacetate is a pleasant smelling compound used in perfumery. Draw structures for each of the intermediates
in the synthesis of ethyl phenylacetate below.
ANSWER:
POINTS: 1
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