Deck 10: Carboxylic Acids and Their Derivatives

Question 1

The IUPAC name for succinic acid is butanedioic acid.What is the structure of succinic acid?

A) CH₃CH₂CH₂CO₂H
B) CH₃CH=CHCO₂H
C) HO₂CCH₂CH₂CO₂H
D) CH₃CH₂CH₂CO₃H
E) HOCH₂CH₂CH₂CO₂H

Answer 1

HO₂CCH₂CH₂CO₂H

Question 2

The boiling point of propanoic acid is higher than that of 1-butanol because:

A) propanoic acid has a higher molecular weight than 1-butanol.
B) propanoic acid is more soluble in water than 1-butanol.
C) propanoic acid is a better hydrogen bond donor than 1-butanol.
D) propanoic acid forms hydrogen bonded dimers and 1-butanol does not.
E) 1-butanol forms hydrogen bonded dimers and propanoic acid does not.

Answer 2

propanoic acid forms hydrogen bonded dimers and 1-butanol does not.

Question 3

The formula for butanoic anhydride is

A)
B)
C)
D)
E)

Answer 3

Question 4

What is a correct name for the following structure?

A) pentanoic acid
B) cyclopentanecarboxylic acid
C) cyclopentanoic acid
D) cyclopentylacetic acid
E) formyl cyclopentane

Question 5

Which structure best describes the double bond character of the amide bond in acetamide?

A) I
B) II
C) III
D) IV
E) V

Question 6

Which of the following carboxylic acids is terephthalic acid?

A) I
B) II
C) III
D) IV
E) V

Question 7

Which of the following molecules would have the highest boiling point?

A) CH₃CO₂H
B) CH₃CH₂OH
C) CH₃CHO
D) CH₃CH=CH₂
E) HCO₂H

Question 8

The IUPAC name for is

A) 2-bromoisopropyl isopropanoate.
B) isopropyl-2-bromoisobutanoate.
C) isopropyl-2-bromo-2-methylpropanoate.
D) 2-bromoisobutanoyl-2-propanoate.
E) isopropyl-2-bromo-3-methylbutanoate.

Question 9

What is the IUPAC name of the following molecule?

A) cyclohexyl propanoate
B) cyclohexyl acetate
C) ethyl cyclohexanoate
D) propyl cyclohexanoate
E) propanoyl cyclohexyl ether

Question 10

Which of the following statements regarding is false?

A) Rotation around the C-N bond is restricted.
B) The carbonyl group, NH group, and both methyl carbons lie in a plane.
C) The nitrogen is strongly basic.
D) The C-N bond is shorter than the C-N bond in amines.
E) The compound is named Nmethylacetamide.

Question 11

Which of the following represents p-bromobenzoic acid?

A)
B)
C)
D)
E)

Question 12

Which of the following molecules is not an anhydride?

A)
B)
C)
D)
E)

Question 13

Which of the following compounds undergoes hydrolysis at the fastest rate upon reaction with sodium hydroxide in water?

A) I
B) II
C) III
D) IV
E) V

Question 14

Rank the following according to their relative acidities

A) 3>2>1
B) 1>2>3
C) 2>3>1
D) 3>1>2
E) 2>1>3

Question 15

The IUPAC name for is

A) potassium 3-bromopropanoate.
B) potassium 2-bromopropanoate.
C) potassium 3-bromopropionate.
D) potassium $\beta$ -bromopropionate.
E) potassium $\gamma$ -bromopropanoate.

Question 16

Which of the following molecules is the weakest acid?

A) CH₃CH₂CO₂H
B) CH₃CH₂CH₃
C) CH₃CH₂OH
D) CH₃CH₂NH₂
E) H₂O

Question 17

Which of the following molecules has the most acidic $\alpha$ -hydrogen?

A)
B)
C)
D)
E)

Question 18

What is the IUPAC name of CH₃CO₂CH(CH₃)₂?

A) ethyl acetate
B) propyl acetate
C) isopropyl ethanoate
D) ethyl propanoate
E) dimethyl acetate

Question 19

What is the name of the following molecule, (CH₃)₂CHCONH₂?

A) 2-methylpropanamide
B) 3-methylpropanamide
C) butyramide
D) ( $\alpha$ -methylbutyramide)
E) methylethanamide

Question 20

What is the common name for CH₃COOH?

A) formic acid
B) acetic acid
C) propionic acid
D) oxalic acid
E) malonic acid

Question 21

The following structure is an intermediate in the reaction of

A)CH₃CO₂CH₃ with HCl.
B)CH₃COCl with CH₃O^- Na⁺.
C)CH₃CO₂CH₃ with HOCl.
D)CH₃CH(OCH₃)₂ with Cl₂.
E)CH₃Cl with (CH₃)₂C=O.

Question 22

Ethyl propanoate can be prepared by the reaction of

A) ethanoic acid with propanol.
B) ethanoic acid with isopropanol.
C) ethanoyl chloride with propanol.
D) propanoyl chloride with ethanol.
E) acetic anhydride with propanol.

Question 23

Which structure represents the tetrahedral intermediate in the following reaction?

A)
B)
C)
D)
E)

Question 24

Oxidation of with KMnO₄

A)
B)
C)
D)
E)

Question 25

The mechanism of saponification is

A) nucleophilic aromatic substitution.
B) nucleophilic acyl substitution.
C) electrophilic aromatic substitution.
D) S_N2.
E) S_N1.

Question 26

Treatment of 1 mole of CH₃CH₂CO₂CH₂CH₃ with 2 moles of Na^{+ -}OCH₂CH₃ followed by the addition of an aqueous solution of acid gives

A)
B)
C)
D)
E) no reaction

Question 27

What is the product of the following reaction sequence?

A)
B)
C)
D)
E)

Question 28

The product(s) from are:

A)
B)
C)
D)
E)

Question 29

The expected product of the reaction is:

A)
B)
C)
D)
E)

Question 30

Saponification of is expected to give:

A)
B)
C)
D)
E)

Question 31

Benzoic acid cannot be prepared by which one of the following methods?

A)
B)
C)
D)
E)

Question 32

The product(s) in the reaction are:

A)
B)
C)
D)
E)

Question 33

Which of the following carbonyl compounds reacts fastest with water?

A) carboxylic acid
B) ester
C) ketone
D) acid chloride
E) amide

Question 34

(CH₃)₃CCO₂H can best be prepared by:

A)
B)
C)
D)
E)

Question 35

The product of the following reaction sequence is:

A)
B)
C)
D)
E)

Question 36

Acid chlorides react with alcohols to give:

A) ketones
B) esters
C) acetals
D) amides
E) carboxylic acids