Question 1

Which of the following statements correctly describes the outcome when a tertiary alcohol is treated with concentrated $$\mathrm{H_2SO_4}$$ under heat?

Accepted Answer

The alcohol undergoes dehydration to form an alkene, following Zaitsev's Rule.

Question 2

Which reagent would you use to selectively oxidize a primary alcohol to an aldehyde without further oxidation to a carboxylic acid?

Accepted Answer

Dess-Martin periodinane

Question 3

Which of the following alcohols will react fastest with $$\mathrm{HBr} to $$form an alkyl bromide?

Accepted Answer

tert-butanol

Question 4

A chemist wants to synthesize 1-phenylethanol from styrene. Which sequence of reactions would achieve this transformation?

Accepted Answer

Hydroboration-oxidation of styrene

Question 5

Which of the following statements about the Williamson Ether Synthesis is correct?

Accepted Answer

It is limited to primary alkyl halides to avoid elimination.

Question 6

When an ether is cleaved by concentrated $$\mathrm{HI}$$, which product is most likely to form if the ether is methyl tert-butyl ether?

Accepted Answer

Iodomethane and tert-butanol

Question 7

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

Accepted Answer

Acid chloride \u003e anhydride \u003e ester \u003e amide

Question 8

Which of the following carboxylic acids would have the lowest pKa?

Accepted Answer

Trifluoroacetic acid

Question 9

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

Accepted Answer

A carboxylic acid

Question 10

Which of the following is a limitation when preparing nitriles from alkyl halides using $$\mathrm{NaCN}$$?

Accepted Answer

Highly substituted alkyl halides tend to undergo elimination rather than substitution.

Question 11

Which protecting group is commonly used for alcohols in multi-step synthesis and can be removed with fluoride ion?

Accepted Answer

Trimethylsilyl (TMS)

Question 12

Which of the following best describes the mechanism of the Fischer esterification?

Accepted Answer

Acid-catalyzed nucleophilic addition-elimination

Question 13

Which reagent would you use to convert a primary alcohol to a primary alkyl bromide?

Accepted Answer

$$\mathrm{$$PBr_3$$}$$

Question 14

What is the major product when 2-methyl-2-butanol is dehydrated with concentrated $$\mathrm{H_2SO_4}$$?

Accepted Answer

2-methyl-2-butene

Question 15

Which of the following is the correct IUPAC name for the compound $$\mathrm{CH_3CH_2COOH}$$?

Accepted Answer

Propanoic acid

Question 16

Which of the following reactions will convert a carboxylic acid to an acid chloride?

Accepted Answer

Reaction with $$\mathrm{$$SOCl_2$$}$$

Question 17

Which of the following statements about amide hydrolysis is correct?

Accepted Answer

It requires either acidic or basic conditions and involves nucleophilic attack at the carbonyl carbon.

Question 18

Which of the following best describes the product of the reaction between a Grignard reagent and carbon dioxide, followed by acidic workup?

Accepted Answer

A carboxylic acid

Question 19

Which of the following is the correct product when benzyl alcohol is oxidized with $$\mathrm{$$CrO_3$$} in $$aqueous acid?

Accepted Answer

Benzoic acid

Question 20

Which of the following is the correct IUPAC name for the compound $$\mathrm{CH_3CH_2CN}$$?

Accepted Answer

Propanenitrile

Alcohols, Ethers, Carboxylic Acids, and Carboxylic Acid Derivatives: Key Concepts and Mechanisms

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