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 sterically hindered and have a more electrophilic carbonyl carbon due to only one alkyl group attached.

Question 2

What is the hybridization and approximate bond angle around the carbonyl carbon in an aldehyde or ketone?

Accepted Answer

$$sp^2$$, approximately $$120^\circ$$

Question 3

A Grignard reagent is prepared by reacting an alkyl halide with which metal in dry ether?

Accepted Answer

Magnesium

Question 4

Which of the following best describes the role of the carbon atom in an organolithium reagent?

Accepted Answer

It acts as a nucleophile due to its partial negative charge.

Question 5

When a Grignard reagent reacts with formaldehyde followed by aqueous workup, what is the major product?

Accepted Answer

A primary alcohol

Question 6

Which of the following reagents can selectively reduce aldehydes and ketones but not carboxylic acids or esters?

Accepted Answer

Sodium borohydride ($$NaBH_4)$$

Question 7

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

Accepted Answer

The nucleophile attacks the less hindered (less substituted) carbon of the epoxide.

Question 8

Which of the following best explains why organometallic reagents must be prepared and used in aprotic solvents?

Accepted Answer

They are very basic and will react with protic solvents, destroying the reagent.

Question 9

A Wittig reaction is used to convert a carbonyl compound into which of the following?

Accepted Answer

An alkene

Question 10

Which of the following is the correct product when methylmagnesium bromide ($$CH_3MgBr) $$reacts with acetone ($$CH_3COCH_3) $$followed by aqueous workup?

Accepted Answer

A tertiary alcohol

Question 11

Which of the following best describes the mechanism of nucleophilic addition to a carbonyl group?

Accepted Answer

The nucleophile attacks the carbonyl carbon, forming a tetrahedral intermediate.

Question 12

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

Accepted Answer

The less substituted the carbonyl carbon, the more reactive it is toward nucleophilic attack.

Question 13

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

$$\mathrm{CH_3CH_2COCH_2CH_3}$$

Accepted Answer

2-pentanone

Question 14

Which of the following statements about the reaction of organocuprate (Gilman) reagents is correct?

Accepted Answer

They react with acid chlorides to give ketones.

Question 15

Which of the following is a typical use of a protecting group in carbonyl chemistry?

Accepted Answer

To prevent unwanted reaction of a carbonyl group during a multi-step synthesis.

Question 16

Which of the following best describes the product of the reaction between a Grignard reagent and carbon dioxide ($$CO_2) $$followed by acid workup?

Accepted Answer

A carboxylic acid

Question 17

Which of the following is the correct order of reactivity toward nucleophilic addition for the following carbonyl compounds: formaldehyde, acetone, benzaldehyde?

Accepted Answer

Formaldehyde \u003e acetone \u003e benzaldehyde

Question 18

Which of the following is a correct statement about the oxidation of primary alcohols?

Accepted Answer

Primary alcohols can be oxidized to aldehydes using PCC.

Question 19

Which of the following is the correct product when 1 equivalent of $$LiAlH_4 is $$added to an ester, followed by aqueous workup?

Accepted Answer

A primary alcohol

Question 20

Which of the following best describes the outcome when a secondary amine reacts with an aldehyde under acidic conditions?

Accepted Answer

An enamine is formed.

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

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