Question 1

Which structural feature of carboxylic acids is responsible for their high boiling points compared to alcohols?

Accepted Answer

Strong hydrogen bonding between acid pairs

Question 2

What is the correct IUPAC name for the following compound: $$\mathrm{CH_3CH_2COOH}$$?

Accepted Answer

Propanoic acid

Question 3

Why are carboxylic acids generally more acidic than alcohols?

Accepted Answer

The conjugate base of carboxylic acids is resonance stabilized

Question 4

Which of the following compounds will have the lowest pKa value?

Accepted Answer

Trichloroacetic acid ($$\mathrm{CCl_3COOH})$$

Question 5

Which method can be used to convert a primary alkyl halide into a carboxylic acid?

Accepted Answer

SN2 reaction with $$\mathrm{CN^-}$$ followed by hydrolysis

Question 6

Why can't Grignard reagents and $$\mathrm{H_3O^+} be $$added together in the carboxylation of a Grignard reaction?

Accepted Answer

Grignard reagents react violently with water

Question 7

Which reagent is used to reduce a carboxylic acid to a primary alcohol?

Accepted Answer

Lithium aluminium hydride ($$\mathrm{$$LiAlH_4$$})$$

Question 8

Which carboxylic acid derivative is the most reactive towards nucleophilic acyl substitution?

Accepted Answer

Acid chloride

Question 9

What is the main difference between nucleophilic acyl substitution and nucleophilic addition to aldehydes/ketones?

Accepted Answer

Carboxylic acid derivatives have a leaving group that can be expelled

Question 10

Which of the following is NOT a typical reaction of acid chlorides?

Accepted Answer

Electrophilic aromatic substitution

Question 11

What is the product when an acid chloride reacts with excess ammonia?

Accepted Answer

Amide

Question 12

Which reagent can be used to selectively reduce an acid chloride to an aldehyde?

Accepted Answer

Lithium tri-tert-butoxy aluminium hydride

Question 13

What is the product of the reaction between an ester and excess $$\mathrm{$$LiAlH_4$$}$$ followed by water?

Accepted Answer

A primary alcohol

Question 14

Which process is used industrially to make soap from fat molecules?

Accepted Answer

Saponification (base-catalyzed hydrolysis)

Question 15

Which carboxylic acid derivative is most commonly found in proteins?

Accepted Answer

Amide

Question 16

What is the product when a nitrile is hydrolyzed under acidic conditions?

Accepted Answer

A carboxylic acid

Question 17

Which reagent is used to convert a nitrile to a ketone via reaction with a Grignard reagent?

Accepted Answer

Grignard reagent followed by aqueous acid

Question 18

Which of the following is a limitation of preparing esters via an SN2 process?

Accepted Answer

Steric hindrance limits the reaction to primary alkyl halides

Question 19

What is the main driving force for nucleophilic acyl substitution reactions?

Accepted Answer

Expulsion of a good leaving group to reform the carbonyl

Question 20

Which of the following statements about nucleophilic acyl substitution is NOT true?

Accepted Answer

Under acidic conditions, the first step is always nucleophilic attack generating both positive and negative charges

Carboxylic Acids and Carboxylic Acid Derivatives: Structure, Properties, Synthesis, and Reactions

Study Guide - Practice Questions