Question 1

Which of the following best explains why aldehydes are generally more reactive toward nucleophilic addition than ketones?

Accepted Answer

Aldehydes have a greater partial positive charge on the carbonyl carbon and less steric hindrance.

Question 2

Arrange the following carbonyl compounds in order of decreasing reactivity toward nucleophilic addition: acyl halide, aldehyde, ketone, carboxylic acid, carboxylate ion.

Accepted Answer

$$1 \u003e 2 \u003e 5 \u003e 4 \u003e 3$$

Question 3

Which reagent will selectively reduce an ester to an aldehyde without further reduction to an alcohol?

Accepted Answer

DIBALH

Question 4

A Grignard reagent reacts with an ester in excess to give which type of alcohol as the final product?

Accepted Answer

Tertiary alcohol

Question 5

Which of the following carbonyl compounds cannot be reduced by NaBH4 under standard conditions?

Accepted Answer

Carboxylic acid

Question 6

What is the product when a ketone reacts with a secondary amine under acidic conditions?

Accepted Answer

Enamine

Question 7

Which of the following statements about the reduction of carboxylic acids with LiAlH4 is correct?

Accepted Answer

The reaction produces a primary alcohol.

Question 8

Which of the following best describes the role of acid in the formation of an acetal from an aldehyde and an alcohol?

Accepted Answer

All of the above.

Question 9

Which reagent(s) will reduce both aldehydes and ketones to alcohols, but not carboxylic acids or esters?

Accepted Answer

NaBH4

Question 10

Which of the following is a correct statement about the Wittig reaction?

Accepted Answer

It forms an alkene from a carbonyl compound and a phosphonium ylide.

Question 11

Which of the following alkyl halides cannot be used to form a phosphonium ylide for the Wittig reaction?

Accepted Answer

A tertiary alkyl halide

Question 12

Which of the following best describes the chemoselectivity of NaBH4?

Accepted Answer

It reduces only aldehydes and ketones, not esters or carboxylic acids.

Question 13

Which product is formed when a cyanohydrin is hydrolyzed under acidic conditions?

Accepted Answer

An alpha-hydroxycarboxylic acid

Question 14

Which of the following reagents will reduce an amide to an amine?

Accepted Answer

LiAlH4

Question 15

Which of the following statements about the reaction of aldehydes and ketones with Grignard reagents is correct?

Accepted Answer

Aldehydes react to give secondary alcohols, ketones give tertiary alcohols.

Question 16

Which of the following is the correct product when an aldehyde reacts with a primary amine under trace acid?

Accepted Answer

An imine

Question 17

Which of the following best describes the product of the Baeyer–Villiger oxidation of a ketone?

Accepted Answer

An ester

Question 18

Which of the following reagents will reduce both the carbonyl group and a carbon–carbon double bond in an α,β-unsaturated ketone?

Accepted Answer

Raney Ni/H2

Question 19

Which of the following is the correct order of priority for naming functional groups in IUPAC nomenclature (highest to lowest) among the following: carboxylic acid, aldehyde, ketone, alcohol?

Accepted Answer

Carboxylic acid \u003e aldehyde \u003e ketone \u003e alcohol

Question 20

Which of the following statements about the reaction of an acyl chloride with a Grignard reagent is correct?

Accepted Answer

The reaction produces a tertiary alcohol after two additions.

Reactions and Properties of Aldehydes and Ketones: Nucleophilic Addition, Reduction, and Synthetic Applications

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