Question 1

Which of the following carboxylic acid derivatives is the most reactive toward nucleophilic acyl substitution?

Accepted Answer

Acid chloride

Question 2

What is the correct IUPAC name for the following compound: $$\mathrm{C_6H_5COBr}$$?

Accepted Answer

Benzoyl bromide

Question 3

Which reagent is commonly used to convert a carboxylic acid to an acid chloride?

Accepted Answer

$$\mathrm{$$SOCl_2$$}$$

Question 4

Which of the following best describes the mechanism of nucleophilic acyl substitution in carboxylic acid derivatives?

Accepted Answer

A two-step process involving a tetrahedral intermediate

Question 5

What is the product when acetyl chloride reacts with excess ammonia ($$\mathrm{NH_3$}$$)?

Accepted Answer

Acetamide

Question 6

Which of the following compounds will have the highest $$^{13}\mathrm{C}$$ NMR chemical shift for the carbonyl carbon?

Accepted Answer

Acetone

Question 7

Which reaction is used to synthesize esters from carboxylic acids and alcohols?

Accepted Answer

Fischer esterification

Question 8

What is the leaving group in the nucleophilic acyl substitution of an acid chloride?

Accepted Answer

$$\mathrm{Cl^-}$$

Question 9

Which IR absorption (in $$\mathrm{cm$$^{-1}$$}) $$would you expect for the carbonyl stretch of an amide?

Accepted Answer

1690

Question 10

Which of the following sequences will convert a carboxylic acid into a primary alcohol?

Accepted Answer

$$1.\ \mathrm{$$LiAlH_4$$}\ 2.\ \mathrm{H_3O^+}$$

Question 11

Which of the following is the correct order of reactivity toward nucleophilic acyl substitution (most to least reactive)?

Accepted Answer

Acid chloride \u003e Acid anhydride \u003e Ester \u003e Amide

Question 12

What is the product of the reaction between ethyl acetate and sodium hydroxide ($$\mathrm{NaOH}) $$under reflux?

Accepted Answer

Sodium acetate and ethanol

Question 13

Which of the following best explains why amides are less reactive than esters toward nucleophilic acyl substitution?

Accepted Answer

The $$\mathrm{NH_2$}$$ group is a poor leaving group and donates electron density to the carbonyl carbon

Question 14

Which product is formed when an acid chloride reacts with a lithium diorganocopper reagent ($$\mathrm{R'_2CuLi}$$)?

Accepted Answer

A ketone

Question 15

What is the major product when acetic anhydride reacts with ethanol?

Accepted Answer

Ethyl acetate

Question 16

Which of the following statements about the Fischer esterification reaction is correct?

Accepted Answer

It is catalyzed by acid and produces water as a byproduct

Question 17

Which of the following is the correct IR absorption range for the carbonyl stretch of an acid anhydride?

Accepted Answer

1820–1760 $$\mathrm{cm$$^{-1}$$}$$

Question 18

Which of the following best describes the product of the reaction between sodium butanoate and methyl iodide?

Accepted Answer

Methyl butanoate

Question 19

What is the expected $$^{13}\mathrm{C}$$ NMR chemical shift (in ppm) for the carbonyl carbon of ethyl acetate?

Accepted Answer

170.7

Question 20

Which of the following is a correct statement about the hydrolysis of acid chlorides?

Accepted Answer

It produces a carboxylic acid and hydrochloric acid

Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions

Study Guide - Practice Questions