Question 1

Which statement best explains why the carbonyl carbon in aldehydes and ketones is susceptible to nucleophilic attack?

Accepted Answer

The carbonyl carbon is partially positive due to the electronegative oxygen withdrawing electron density.

Question 2

Which of the following carbonyl compounds is most reactive toward nucleophilic attack?

Accepted Answer

Formaldehyde

Question 3

What is the correct IUPAC name for the following structure: $$\mathrm{CH_3CH_2COCH_3}$$?

Accepted Answer

Butan-2-one

Question 4

Why are ketones generally less reactive than aldehydes in nucleophilic addition reactions?

Accepted Answer

Ketones have more steric hindrance and less partial positive charge on the carbonyl carbon.

Question 5

Which reagent is commonly used to selectively reduce aldehydes and ketones to alcohols, but not esters or carboxylic acids?

Accepted Answer

NaBH4

Question 6

A Grignard reagent reacts with formaldehyde. What is the major organic product after aqueous workup?

Accepted Answer

A primary alcohol

Question 7

Which of the following is a correct general reaction for the preparation of an organolithium reagent?

Accepted Answer

$$\mathrm{R-X + 2Li \rightarrow R-Li + LiX}$$

Question 8

What is the product when a Gilman reagent ($$\mathrm{R_2CuLi}) $$reacts with an acid chloride ($$\mathrm{R'-COCl}$$)?

Accepted Answer

$$\mathrm{R'-COR}$$

Question 9

Which statement about the reaction of organometallic reagents with epoxides is correct?

Accepted Answer

The nucleophile attacks the less hindered side of the epoxide.

Question 10

Which of the following best describes the role of a protecting group in carbonyl chemistry?

Accepted Answer

It temporarily blocks the carbonyl group from reacting with nucleophiles.

Question 11

What is the major product when a Grignard reagent reacts with acetone followed by aqueous workup?

Accepted Answer

A tertiary alcohol

Question 12

Which of the following is true about the Wittig reaction?

Accepted Answer

It converts a carbonyl group into an alkene using a phosphonium ylide.

Question 13

Which of the following is the correct mechanism for nucleophilic addition to a carbonyl group?

Accepted Answer

Nucleophile attacks the carbonyl carbon, forming a tetrahedral intermediate.

Question 14

Which of the following statements about organometallic reagents is correct?

Accepted Answer

They are strong nucleophiles and react rapidly with carbonyl compounds.

Question 15

What is the expected product when methylmagnesium bromide reacts with cyclopentanecarbaldehyde followed by acid workup?

Accepted Answer

2-methylcyclopentanol

Question 16

Which of the following is a correct statement about the reactivity of carbonyl compounds?

Accepted Answer

Steric hindrance decreases the reactivity of the carbonyl carbon.

Question 17

Which of the following is the correct product of the reaction between an organolithium reagent and carbon dioxide followed by acid workup?

Accepted Answer

A carboxylic acid

Question 18

What is the effect of conjugation on the reactivity of a carbonyl group?

Accepted Answer

Conjugation decreases the reactivity of the carbonyl group.

Question 19

Which of the following is a correct statement about the use of protecting groups in organic synthesis?

Accepted Answer

Protecting groups are used to temporarily mask reactive functional groups during multi-step synthesis.

Organometallics and Reactions of Aldehydes & Ketones: Structure, Reactivity, and Mechanisms

Study Guide - Practice Questions