Chapter 20 - Carboxylic Acid Derivatives_ Nucleophilic Substitution (Test Bank)

1. What is the name of the following ester?




A. propyl ethanoate
B. ethyl propanoate
C. ethoxy butanoate
D. ethyl butanoate

Bloom's Level: 3. Apply
Chapter: 20
Difficulty: Medium
Gradable: automatic
Section: 20.01
Subtopic: IUPAC nomenclature of carboxylic acids and carboxylic acid derivatives
Topic: Carboxylic Acids and Carboxylic Acid Derivatives


2. Which of the following is isopropyl benzoate?

A. C6H5CO2CH(CH3)2
B. C6H5CH2CO2CH(CH3)2
C. (CH3)2CHCO2C6H5
D. (CH3)2CHCO2CH2C6H5

Accessibility: Keyboard Navigation
Bloom's Level: 3. Apply
Chapter: 20
Difficulty: Medium
Gradable: automatic
Section: 20.01
Subtopic: IUPAC nomenclature of carboxylic acids and carboxylic acid derivatives
Topic: Carboxylic Acids and Carboxylic Acid Derivatives




20-1
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,3. What is the name of the following compound?




A. 2-chlorohexyl ethanoate
B. 1-chlorohexyl ethanoate
C. ethyl 2-chlorohexanoate
D. ethyl 1-chlorohexanoate

Bloom's Level: 3. Apply
Chapter: 20
Difficulty: Medium
Gradable: automatic
Section: 20.01
Subtopic: IUPAC nomenclature of carboxylic acids and carboxylic acid derivatives
Topic: Carboxylic Acids and Carboxylic Acid Derivatives


4. What is the name of the compound shown below?




A. 2-bromo-N-methylpentanamide
B. 2-bromo(methylamino)pentanamide
C. methylamino 2-bromopentanamide
D. methyl 2-bromopentanamide

Bloom's Level: 3. Apply
Chapter: 20
Difficulty: Medium
Gradable: automatic
Section: 20.01
Subtopic: IUPAC nomenclature of carboxylic acids and carboxylic acid derivatives
Topic: Carboxylic Acids and Carboxylic Acid Derivatives




20-2
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McGraw-Hill Education.

,5. Which of the following has the fastest rate of hydrolysis to give acetic acid?




A. A
B. B
C. C
D. D

Bloom's Level: 4. Analyze
Chapter: 20
Difficulty: Easy
Gradable: automatic
Section: 20.02
Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives
Topic: Carboxylic Acids and Carboxylic Acid Derivatives


6. The compound shown below is classified as a(n)




A. lactone.
B. β-ketoester.
C. diketone.
D. carboxylic acid anhydride.

Bloom's Level: 2. Understand
Chapter: 20
Difficulty: Easy
Gradable: automatic
Section: 20.01
Subtopic: IUPAC nomenclature of carboxylic acids and carboxylic acid derivatives
Topic: Carboxylic Acids and Carboxylic Acid Derivatives




20-3
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.

, 7.
Rank the following in order of decreasing rate of hydrolysis.

I. acetyl chloride

II. acetic anhydride

III. ethyl acetate

IV. acetamide



A. I > II > III > IV
B. I > III > II > IV
C. IV > III > II > I
D. II > III > IV > I

Accessibility: Keyboard Navigation
Bloom's Level: 4. Analyze
Chapter: 20
Difficulty: Medium
Gradable: automatic
Section: 20.02
Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives
Topic: Carboxylic Acids and Carboxylic Acid Derivatives




8. How are reactions between aldehydes and nucleophiles fundamentally different than
reactions between acyl chlorides and nucleophiles?
A. Aldehydes are readily oxidized by nucleophiles to carboxylic acids.
B. Acyl chlorides have a leaving group, Cl¯, whereas aldehydes do not.
C. Aldehydes do not form tetrahedral intermediates with nucleophiles.
D. Acyl chlorides readily form enol tautomers.

Accessibility: Keyboard Navigation
Bloom's Level: 2. Understand
Chapter: 20
Difficulty: Medium
Gradable: automatic
Section: 20.03
Subtopic: Reactions of carboxylic acids and carboxylic acid derivatives
Topic: Carboxylic Acids and Carboxylic Acid Derivatives




20-4
Copyright © 2016 McGraw-Hill Education. All rights reserved. No reproduction or distribution without the prior written consent of
McGraw-Hill Education.