Question 1

Which reagent is used to convert an alkyl halide to a carboxylic acid via carbonation, as shown in the reaction of cyclopentylmagnesium bromide with carbon dioxide?

Accepted Answer

Grignard reagent (RMgBr)

Question 2

What is the product when 3-cyclopentene-carboxylic acid is treated with LiAlH4 in ether followed by water?

Accepted Answer

4-Hydroxymethylcyclopentene

Question 3

Which functional group is selectively reduced by NaBH4 in the presence of a carboxylic acid group, as shown in the reduction of 5-oxo-5-phenylpentanoic acid?

Accepted Answer

Aldehyde or ketone

Question 4

In Fischer esterification, which acid catalyst is commonly used to convert ethanoic acid and ethanol to ethyl ethanoate?

Accepted Answer

H2SO4

Question 5

What is the product when butanoic acid reacts with thionyl chloride (SOCl2)?

Accepted Answer

Butanoyl chloride

Question 6

Arrange the following carboxylic acid derivatives in order of increasing reactivity toward nucleophilic acyl substitution: amide, ester, anhydride, acid halide.

Accepted Answer

Amide \u003c Ester \u003c Anhydride \u003c Acid halide

Question 7

Which leaving group has the greatest leaving ability in nucleophilic acyl substitution reactions?

Accepted Answer

$$\mathrm{X^-}$$

Question 8

Which carboxylic acid derivative reacts most rapidly with water to form a carboxylic acid?

Accepted Answer

Acid halide

Question 9

What is the main difference between acid-catalyzed and base-catalyzed hydrolysis of esters?

Accepted Answer

Acid hydrolysis is reversible, base hydrolysis is irreversible

Question 10

Which product is formed when acetyl chloride reacts with water?

Accepted Answer

Acetic acid

Question 11

What is the product of hydrolysis of acetic anhydride with water?

Accepted Answer

Two molecules of acetic acid

Question 12

Which reagent is used to convert butanoyl chloride and cyclohexanol to cyclohexyl butanoate?

Accepted Answer

No catalyst is necessary

Question 13

Why is pyridine used in the reaction of benzoyl chloride with 3-methyl-1-butanol?

Accepted Answer

To neutralize the HCl formed

Question 14

Aspirin is synthesized by treating salicylic acid with which reagent?

Accepted Answer

Acetic anhydride

Question 15

What is the product when hexanoyl chloride reacts with two moles of ammonia?

Accepted Answer

Hexanamide and ammonium chloride

Question 16

Which reagent is used to reduce an ester to an aldehyde at low temperature?

Accepted Answer

DIBALH

Question 17

What is the product when octanamide is reduced with LiAlH4 followed by water?

Accepted Answer

1-Octanamine

Question 18

Which step occurs first in the reduction of an amide by LiAlH4?

Accepted Answer

Addition of hydride ion to the carbonyl carbon

Question 19

Which product is formed when methyl hexanoate is treated with DIBALH at $$-78^\circC $$followed by water?

Accepted Answer

Hexanal

Question 20

Which carboxylic acid derivative is least reactive toward nucleophilic acyl substitution?

Accepted Answer

Amide

Carboxylic Acids and Their Derivatives: Preparation, Reactions, and Mechanisms

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