Question 1

Which of the following statements best explains why carboxylic acids have higher boiling points than alcohols and alkanes of similar molecular weight?

Accepted Answer

Carboxylic acids can form stronger hydrogen bonds due to the presence of both a carbonyl and hydroxyl group.

Question 2

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

Accepted Answer

Propanoic acid

Question 3

Which of the following carboxylic acids is expected to be the most acidic?

Accepted Answer

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

Question 4

Which reagent would you use to convert a primary alcohol to a carboxylic acid?

Accepted Answer

$$\mathrm{Na_2Cr_2O_7}$$, $$\mathrm{H_2SO_4}$$

Question 5

Which of the following best describes the effect of an electron-withdrawing group on the acidity of a carboxylic acid?

Accepted Answer

It increases the acidity by stabilizing the conjugate base through the inductive effect.

Question 6

Which of the following is the correct product when butanoic acid reacts with potassium hydroxide ($$\mathrm{KOH}$$)?

Accepted Answer

Potassium butanoate ($$\mathrm{CH_3CH_2CH_2COOK})$$

Question 7

Which method would you use to synthesize a carboxylic acid from a Grignard reagent?

Accepted Answer

React the Grignard reagent with carbon dioxide ($$\mathrm{CO_2$}) $$followed by acidic workup.

Question 8

Which of the following is the correct sequence of reagents to convert a carboxylic acid to an aldehyde?

Accepted Answer

$$\mathrm{$$SOCl_2$$}$$, then $$\mathrm{LiAlH(O-tBu)_3}$$

Question 9

Which of the following is the correct product of the Fischer esterification of acetic acid ($$\mathrm{CH_3COOH}) $$with ethanol ($$\mathrm{CH_3CH_2OH}$$)?

Accepted Answer

Ethyl acetate ($$\mathrm{CH_3COOCH_2CH_3})$$

Question 10

Which of the following statements about the solubility of carboxylic acid salts is correct?

Accepted Answer

Carboxylic acid salts of alkali metals are generally soluble in water.

Question 11

Which of the following is the correct mechanism for the formation of an ester from a carboxylic acid and an alcohol under acidic conditions?

Accepted Answer

Nucleophilic attack of the alcohol on the protonated carbonyl carbon, followed by loss of water.

Question 12

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

Accepted Answer

Thionyl chloride ($$\mathrm{$$SOCl_2$$})$$

Question 13

Which of the following reactions will produce a carboxylic acid from an alkene?

Accepted Answer

Oxidative cleavage with $$\mathrm{$$KMnO_4$$} ($$warm)

Question 14

Which of the following is the correct product when benzoic acid reacts with $$\mathrm{KOH}$$?

Accepted Answer

Potassium benzoate ($$\mathrm{C_6H_5COOK})$$

Question 15

Which of the following statements is true regarding the reduction of carboxylic acids with $$\mathrm{$$LiAlH_4$$}$$?

Accepted Answer

Carboxylic acids are reduced to primary alcohols.

Question 16

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

$$\mathrm{BrCH_2CH_2COOH}$$

Accepted Answer

2-bromopropanoic acid

Question 17

Which of the following is a correct statement about the effect of the position of an electron-withdrawing group on the acidity of a carboxylic acid?

Accepted Answer

The closer the electron-withdrawing group is to the COOH group, the greater its effect on acidity.

Question 18

Which of the following is the correct product when an acid chloride reacts with an amine ($$\mathrm{R'NH_2$}$$)?

Accepted Answer

Amide ($$\mathrm{RCONHR'})$$

Question 19

A student wants to synthesize ethanoic acid from bromoethane. Which sequence of reactions would achieve this transformation?

Accepted Answer

Convert bromoethane to a Grignard reagent, react with $$\mathrm{CO_2$}$$, then acidic workup.

Chapter 20 Carboxylic Acids

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