Question 1

Which of the following statements best describes the bonding and structure of the carbonyl group in aldehydes and ketones?

Accepted Answer

The carbonyl carbon is sp$$^2$$ hybridized, and the bond angle is approximately 120°.

Question 2

Which of the following compounds is correctly matched with its common name?

Accepted Answer

CH$$_3$$COCH$$_3$$: Acetone

Question 3

Which of the following best explains why aldehydes generally have higher boiling points than alkanes of similar molecular weight, but lower than alcohols?

Accepted Answer

Aldehydes have a polar C=O bond, leading to dipole-dipole interactions, but cannot hydrogen bond with themselves.

Question 4

Which IR absorption is most characteristic for the C=O stretch in a simple, unconjugated ketone?

Accepted Answer

$$1715\ 	ext{cm}^{-1}$$

Question 5

Which of the following reactions is best for synthesizing a phenyl ketone such as acetophenone?

Accepted Answer

Friedel-Crafts Acylation

Question 6

A chemist wants to selectively oxidize a primary alcohol to an aldehyde without further oxidation to a carboxylic acid. Which reagent should be used?

Accepted Answer

PCC (Pyridinium chlorochromate)

Question 7

Which of the following statements about the McLafferty rearrangement in mass spectrometry is correct?

Accepted Answer

It is a common fragmentation for aldehydes and ketones with a gamma hydrogen.

Question 8

Which of the following is the correct product when a Grignard reagent reacts with a nitrile, followed by hydrolysis?

Accepted Answer

A ketone

Question 9

Which reducing agent is weak enough to reduce an acid chloride to an aldehyde without further reduction to a primary alcohol?

Accepted Answer

DIBAL-H (Diisobutylaluminum hydride)

Question 10

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

Accepted Answer

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

Question 11

Which compound will react fastest with water to form a hydrate?

Accepted Answer

Formaldehyde

Question 12

What is the structure formed when an aldehyde reacts with HCN (hydrogen cyanide)?

Accepted Answer

A cyanohydrin

Question 13

Which of the following is required to form an imine from a ketone?

Accepted Answer

A primary amine and acid catalyst

Question 14

Which of the following is the correct structure for an oxime?

Accepted Answer

R$$_2C=$$NOH

Question 15

Why will an acetal not form from a ketone in basic conditions?

Accepted Answer

The base deprotonates the alcohol, preventing the formation of the required oxonium ion intermediate.

Question 16

Which of the following best describes the Wittig reaction?

Accepted Answer

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

Question 17

Which reagent is used in the Tollens test to detect aldehydes?

Accepted Answer

Ag(NH$$_3$$)$$_2^+ ($$silver ammonia complex)

Question 18

Which of the following is the product when benzaldehyde is treated with NaBH$$_4$$?

Accepted Answer

Benzyl alcohol

Question 19

Which of the following best describes the outcome of the Wolff-Kishner reduction?

Accepted Answer

Aldehyde or ketone is converted to an alkane

Aldehydes and Ketones: Structure, Properties, Synthesis, and Reactions (Chapter 18 Study Guide)

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