Question 1

Which of the following best describes the mechanism by which carboxylic acids react with alcohols in the Fischer esterification?

Accepted Answer

Nucleophilic acyl substitution where the alcohol replaces the hydroxyl group of the acid

Question 2

What is the correct IUPAC name for the following compound: $$\mathrm{CH_3CH_2CHBrCOOH}$$?

Accepted Answer

2-bromobutanoic acid

Question 3

Which reagent would selectively reduce a carboxylic acid to a primary alcohol without affecting a ketone group present in the same molecule?

Accepted Answer

Borane ($$\mathrm{BH_3$})$$

Question 4

Which of the following is the correct order of reactivity toward nucleophilic acyl substitution for carboxylic acid derivatives?

Accepted Answer

Acid chloride \u003e Anhydride \u003e Ester \u003e Amide \u003e Carboxylate

Question 5

A student wants to synthesize N-phenylbenzamide ($$\mathrm{PhCONHPh}) $$from benzoic acid and aniline. Which sequence of reagents should be used?

Accepted Answer

1. $$\mathrm{$$SOCl_2$$}$$, 2. $$\mathrm{$$PhNH_2$$}$$

Question 6

Which of the following reactions will occur rapidly under mild conditions?

Accepted Answer

$$\mathrm{PhCOCl + CH_3NH_2 \rightarrow $$PhCONHCH_3$$ + HCl}$$

Question 7

What is the product when ethyl propionate ($$\mathrm{CH_3CH_2COOCH_2CH_3}) is $$treated with sodium hydroxide?

Accepted Answer

Sodium propionate and ethanol

Question 8

Which of the following best explains why acid chlorides are more reactive than amides toward nucleophilic acyl substitution?

Accepted Answer

Chloride is a better leaving group than amide

Question 9

Which of the following is the correct product of the reduction of benzoic acid with lithium aluminum hydride ($$\mathrm{$$LiAlH_4$$}) $$followed by water?

Accepted Answer

Benzyl alcohol ($$\mathrm{C_6H_5CH_2OH})$$

Question 10

Which method would you use to synthesize methyl cyclohexyl ketone from cyclohexanecarboxylic acid?

Accepted Answer

Convert to acid chloride, react with methyl lithium

Question 11

Which of the following is the correct structure for isoamyl acetate (banana oil)?

Accepted Answer

$$\mathrm{CH_3COOCH_2CH_2CH(CH_3$)_2}$$

Question 12

Which of the following best describes the product of the reaction: $$\mathrm{RCOCl + H_2O \rightarrow}$$ ?

Accepted Answer

Carboxylic acid and HCl

Question 13

Which of the following is a correct method to drive the Fischer esterification to completion when synthesizing methyl formate (bp 32°C)?

Accepted Answer

Distill off the methyl formate as it forms

Question 14

Which of the following is the correct IUPAC name for the compound shown below?

(a) $$\mathrm{CH_3CH_2CH(CH_3$)COOH}$$

Accepted Answer

3-methylbutanoic acid

Question 15

Which of the following best describes the product of the reaction between benzoic acid and thionyl chloride ($$\mathrm{$$SOCl_2$$}$$)?

Accepted Answer

Benzoyl chloride ($$\mathrm{C_6H_5COCl})$$

Question 16

Which of the following is the correct product when an ester is treated with two equivalents of a Grignard reagent followed by acid workup?

Accepted Answer

A tertiary alcohol

Question 17

Which of the following is the correct IUPAC name for the compound with the structure shown below?

(c) Benzene ring with three nitro groups at positions 2, 4, and 6, and a carboxylic acid group at position 1.

Accepted Answer

2,4,6-trinitrobenzoic acid

Question 18

Which of the following best describes the mechanism of base-catalyzed hydrolysis (saponification) of an ester?

Accepted Answer

Nucleophilic attack by hydroxide ion, formation of a tetrahedral intermediate, elimination of alkoxide, and proton transfer

Carboxylic Acids and Their Derivatives: Structure, Nomenclature, Synthesis, and Reactivity

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