Deck 15: Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

Question 1

Which of the following compounds is N,N-dimethylbenzamide?

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

Answer 1

V

Question 2

What is the IUPAC name for the following compound?

A)3-methylpentanoic acid
B)isohexanoic acid
C)β-methylvaleric acid
D)2-methylpentanoic acid
E)3-methylvaleric acid

Answer 2

3-methylpentanoic acid

Question 3

Which of the following compounds is D-valerolactam?

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

Answer 3

V

Question 4

What is the IUPAC name for the following compound?

A)phenyl acetate
B)methyl benzoate
C)methyl phenylacetate
D)benzyl acetate
E)benzyl methylacetate

Question 5

Provide the proper IUPAC name for (CH₃)₃CCH₂CH₂CH(CN)CH₃.

Question 6

Which of the following compounds is an anhydride?

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

Question 7

What is the common name for the following compound?

A)propanoic anhydride
B)formic anhydride
C)formyl formate
D)ethanoic anhydride
E)diformyl ether

Question 8

Which of the following compounds is an acyl chloride?

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

Question 9

What is the common name for the following compound?

A)benzonitrile
B)benzenecyanide
C)phenylcyanide
D)cyanophenyl
E)benzocyanide

Question 10

Which of the following compounds is g-butyrolactone?

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

Question 11

Provide the structure of propanoic anhydride.

Question 12

Provide the proper IUPAC name for ClCH₂CH₂CONHCH₃.

Question 13

Which of the following compounds is an amide?

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

Question 14

Which of the following compounds is an ester?

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

Question 15

Which of the following compounds is methyl formate?

A)
B)
C)
D)
E)

Question 16

Provide the proper IUPAC name for the compound below.

Question 17

Provide the proper IUPAC name for the compound below.

Question 18

Which of the following compounds is benzoyl chloride?

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

Question 19

What is the common name for the following compound?

A)phenylcarbamide
B)benzamide
C)phenylmethanamide
D)benzeneamide
E)benzylamide

Question 20

What is the common name for the following compound?

A)λ-chlorobutanoic acid
B)β-chlorobutanoic acid
C)β-chlorobutyric acid
D)λ-chlorobutyric acid
E)3-chlorobutyric acid

Question 21

Arrange the compounds below in order of increasing boiling point.

Question 22

Give the systematic name of the structure.

A)3-methylpentanenitrile
B)2-methylpentanenitrile
C)2-methylbutanenitrile
D)3-methylbutanenitrile
E)3-methylpentylnitrile

Question 23

Give the name of the structure.

A)1,3-dichloropentanoate
B)3-chloropentanoyl chloride
C)2-chloropentyl chloride
D)2-chloropentanoyl chloride
E)2-chlorobutanoyl chloride

Question 24

Give the name of the structure.

A)Z-2-methyl-2-pentanoic acid
B)E-2-methyl-2-pentanoic acid
C)Z-2-methyl-2-pentenoic acid
D)E-2-methyl-2-pentenoic acid
E)E-2-methyl-2-pentynoic acid

Question 25

Give the name of the structure.

A)N,2-dimethylpentanamide
B)isopentyl methyl amide
C)N,2-dimethylbutanamide
D)N,3-dimethylbutanamide
E)N,3-dimethylpentanamide

Question 26

Provide the IUPAC name for the organic compound below.

Question 27

Which of the following compounds has the lowest boiling point?

A)1-butanol
B)butanoic acid
C)butanenitrile
D)methyl propanoate
E)butanamide

Question 28

Which reaction coordinate diagram best represents the reaction that occurs when NaNH₂ reacts with CH₃COCl to form acetamide?

A)
B)
C)
D)
E)

Question 29

Provide the IUPAC name for the organic compound below.

Question 30

What is the hybridization and geometry of the carbonyl carbon in carboxylic acids and their derivatives?

A)sp³,tetrahedral
B)sp²,trigonal planar
C)sp²,tetrahedral
D)sp³,trigonal planar
E)sp,trigonal planar

Question 31

Give the name of the structure.

A)amino propanoate
B)ammonium butanoate
C)amino butanoate
D)ammonium propanoate
E)propyl amine

Question 32

Give the systematic name of the structure.

Question 33

Provide the IUPAC name for the organic compound below.

Question 34

Provide the name of the compound below.

Question 35

Provide the systematic name of the compound shown below.

Question 36

Give the name of the structure.

A)ethyl butanoate
B)butyl methyl ether
C)ethyl pentanoate
D)butyl ethanoate
E)pentyl ethanoate

Question 37

Give the name of the structure.

A)butanoic ethanoic anhydride
B)butanoic propanoic anhydride
C)ethanoic pentanoic anhydride
D)pentyl propyl anhydride
E)pentanoic propanoic anhydride

Question 38

In which of the following compounds does the carbonyl stretch in the IR spectrum occur at the lowest wavenumber?

A)cyclohexanone
B)ethyl acetate
C)propanoyl chloride
D)pentanamide
E)λ-butyrolactone

Question 39

Which C-N bond below is shorter,I or II? Explain.

Question 40

Give the name of the structure.

A)4-methyl-2-oxacyclohexanone
B)5-methyl-2-oxacyclohexanone
C)3-methyl-2-oxacyclohexanone
D)4-methyl-2-oxacyclopentanone
E)3-methyl-2-oxacyclopentanone

Question 41

List the following carboxylic acid derivatives in decreasing order of reactivity in nucleophilic acyl substitution reactions: acetic anhydride,methyl acetate,acetamide,acetyl chloride.

Question 42

Give the product of the reaction.

A)
B)
C)
D)
E)

Question 43

Provide the structure of the tetrahedral intermediate in the reaction of sodium methoxide with propanoyl chloride.

Question 44

Which of the following compounds is hydrolyzed most rapidly in aqueous NaOH?

A)
B)
C)
D)
E)

Question 45

Which of the following compounds would yield acetic acid when hydrolyzed under heat?

A)
B)CH₃C N
C)
D)
E)all the above

Question 46

Which of the following is the best method for preparing

A)
B)
C)
D)
E)

Question 47

In the lab,a student tried to prepare N,N-diethylacetamide by heating acetyl chloride with two equivalents of triethylamine.Was the student successful? Explain.

Question 48

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

A)
B)
C)
D)
E)

Question 49

Which of the following compounds is hydrolyzed most slowly in aqueous NaOH?

A)
B)
C)
D)
E)

Question 50

Give the product of the reaction.

A)
B)
C)
D)
E)

Question 51

Typically,amides will hydrolyze under ________ conditions than esters.

A)milder
B)more dilute
C)more vigorous
D)less vigorous
E)more saline

Question 52

Do you expect the following reaction to go to completion? Why or why not?

Question 53

Provide a detailed,stepwise mechanism for the reaction of propanoyl chloride with ammonia.

Question 54

Acetyl chloride undergoes nucleophilic substitution at a faster rate than methyl acetate because

A)the ester is more sterically hindered than the acid chloride.
B)the acid chloride is more sterically hindered than the ester.
C)the methoxide is a better leaving group than chloride.
D)esters hydrolyze faster than acid chlorides.
E)chloride is a better leaving group than methoxide.

Question 55

What are the products from the following reaction?

Question 56

Provide a detailed,stepwise mechanism for the reaction of acetyl chloride with methanol to produce methyl acetate and HCl.

Question 57

When benzoyl chloride is reacted with ammonia to prepare benzamide,two equivalents of ammonia must be used.Explain why this is the case.

Question 58

Esters and amides are most easily made by nucleophilic acyl substitution reactions on

A)alcohols.
B)acid anhydrides.
C)carboxylates.
D)carboxylic acids.
E)acid chlorides.

Question 59

Which of the following compounds is the least reactive toward nucleophilic acyl substitution?

A)
B)
C)
D)
E)

Question 60

In nucleophilic acyl substitution

A)protonation of the carbonyl is followed immediately by loss of the leaving group.
B)loss of the leaving group is followed by rearrangement of the carbocation.
C)addition to the carbonyl by a nucleophile is followed by loss of the leaving group.
D)ester hydrolysis is followed by deprotonation.
E)an S_N2 reaction occurs.

Question 61

Give the product of the reaction.

A)
B)
C)
D)
E)

Question 62

Provide the major organic product of the following.

Question 63

Provide a detailed,stepwise mechanism for the acid-catalyzed transesterification of ethyl acetate with n-propanol.

Question 64

Which of the following is one of the steps in the mechanism of the following reaction?

A)
B)
C)
D)
E)

Question 65

Give the products of the reaction.

Question 66

Provide the major organic product of the following reaction.

Question 67

Which of the following is formed in the reaction between ethyl butanoate and ethyl amine?

A)ethanol
B)1-butanol
C)N-ethylbutanamide
D)both A and C
E)both B and C

Question 68

What is the product obtained from the following reaction?

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

Question 69

Provide the major organic product of the reaction below.

Question 70

The hydrolysis of esters in base is called

A)the Fischer esterification.
B)the Hunsdiecker reaction.
C)the Dieckmann condensation.
D)transesterification.
E)saponification.

Question 71

Provide the major organic product of the following reaction.

Question 72

Provide the major organic product of the reaction below.

Question 73

Which of the following intermediates is present in the acid-catalyzed hydrolysis of t-butylacetate but not in the acid-catalyzed hydrolysis of methyl acetate?

A)a protonated carbonyl
B)a carbocation
C)a carbanion
D)a carboxylate anion
E)1-propanol

Question 74

A wax is an ester formed from a long-chain carboxylic acid and a long-chain alcohol.Show how a wax can be made by using CH₃(CH₂)₁₅OH as the only organic starting material.

Question 75

Provide the major organic product of the following.

Question 76

Provide the major organic product of the following.

Question 77

Provide the major organic product of the reaction below.

Question 78

Which of the following esters undergoes hydrolysis in base most easily?

A)CH₃CH₂CO₂CH₃
B)(CH₃)₂CHCH₂CO₂CH₃
C)C₆H₅O₂CCH₃
D)p-CH₃C₆H₄O₂CCH₃
E)p-NO₂C₆H₄O₂CCH₃

Question 79

Provide a detailed,stepwise mechanism for the reaction of butyrolactone with ammonia.

Question 80

Provide a detailed,stepwise mechanism for the base-mediated transesterification of methyl benzoate with sodium ethoxide.