Question 1

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

Accepted Answer

Aldehydes are less stable and less crowded than ketones.

Question 2

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

Accepted Answer

$$\mathrm{RCOCl} ($$acid chloride)

Question 3

What is the product when an acid chloride is treated with $$\mathrm{$$LiAlH_4$$}$$ followed by water?

Accepted Answer

A primary alcohol

Question 4

Which reagent would selectively reduce an acid chloride to an aldehyde without further reduction to an alcohol?

Accepted Answer

$$\mathrm{LiAlH[OC(CH_3$)_3]_3}$$

Question 5

Which of the following statements about nucleophilic addition to carbonyl compounds is correct?

Accepted Answer

Aldehydes and ketones undergo nucleophilic addition to form alcohols.

Question 6

Which organometallic reagent would you use to convert an acid chloride to a ketone without further reaction to a tertiary alcohol?

Accepted Answer

Organocuprate reagent ($$\mathrm{R_2CuLi})$$

Question 7

A chemist wants to prepare a 1° alcohol from an aldehyde. Which reagent should be used?

Accepted Answer

$$\mathrm{$$LiAlH_4$$}$$ followed by $$\mathrm{H_2O}$$

Question 8

Which of the following statements about the reaction of organometallic reagents with esters is correct?

Accepted Answer

Two equivalents of Grignard reagent convert an ester to a tertiary alcohol.

Question 9

Which of the following best describes the product of the reaction between a ketone and a Grignard reagent followed by water?

Accepted Answer

A tertiary alcohol

Question 10

Which of the following carbonyl compounds will react most rapidly with a nucleophile?

Accepted Answer

An acid chloride

Question 11

Which of the following is a limitation of organometallic reagents in synthesis?

Accepted Answer

They react with molecules containing N—H or O—H bonds.

Question 12

Which reagent is commonly used to oxidize aldehydes to carboxylic acids?

Accepted Answer

$$\mathrm{Na_2Cr_2O_7}$$

Question 13

Which of the following best describes the product of the reaction between an α,β-unsaturated carbonyl compound and an organocuprate reagent?

Accepted Answer

A 1,4-addition product

Question 14

A chemist treats a ketone with $$\mathrm{PhLi}$$ followed by water. What is the major product?

Accepted Answer

A tertiary alcohol with a phenyl group attached

Question 15

Which of the following is true regarding the reactivity of carbonyl compounds toward nucleophilic substitution?

Accepted Answer

Esters and carboxylic acids have similar reactivity.

Question 16

Which of the following best describes the mechanism when a nucleophile reacts with a carbonyl compound containing a good leaving group?

Accepted Answer

Nucleophilic substitution

Question 17

Which of the following reagents would you use to selectively oxidize an aldehyde in the presence of other functional groups?

Accepted Answer

$$\mathrm{Ag_2O, NH_4OH} ($$Tollen’s reagent)

Question 18

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

Accepted Answer

Organometallic reagents open epoxides to give alcohols with a new carbon–carbon bond.

Question 19

Which of the following best describes the product of the reaction between an ester and two equivalents of a Grignard reagent followed by water?

Accepted Answer

A tertiary alcohol

Chapter 17: Introduction to Carbonyl Chemistry and Organometallic Reactions

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