Deck 21: Carboxylic Acid Derivatives

Question 1

Provide the proper IUPAC name for the compound below.

Answer 1

3,3-dimethylcyclobutanecarbonitrile

Question 2

Provide the IUPAC name of the following compound.

Answer 2

ethyl hexanoate

Question 3

Cyclic amides are called:

A) lactones.
B) lactams.
C) aminals.
D) animals.
E) imines.

Answer 3

lactams.

Question 4

The correct priority of functional groups in IUPAC nomenclature is:

A) ester > amide > ketone > acid.
B) ketone > acid > ester > amide.
C) acid > ester > amide > ketone.
D) amide > acid > ester > ketone.
E) amide > ester > acid > ketone.

Question 5

Provide the structure of cyclohexyl formate.

Question 6

Provide the proper IUPAC name for ClCH₂CH₂CONHCH₃.

Question 7

Provide the proper IUPAC name for the compound below.

Question 8

Provide the name of the compound shown below.

Question 9

Provide the structure of trifluoroacetic anhydride.

Question 10

Provide the structure of propanoic anhydride.

Question 11

Amides are less basic than amines because:

A) the carbonyl group donates electrons by resonance.
B) the carbonyl group withdraws electrons by resonance.
C) the nitrogen does not have a lone pair of electrons.
D) the nitrogen has a full positive charge.
E) amides do not contain nitrogen.

Question 12

N-Methylacetamide is an example of:

A) a primary amide.
B) a secondary amide.
C) a tertiary amide.
D) an N, N-disubstituted amide.
E) an imine

Question 13

Provide the name of the compound shown below.

Question 14

Which of the following structures are carboxylic acid derivatives?

A) 3
B) 1 & 3
C) 1, 2, & 3
D) 4
E) All are carboxylic acid derivatives.

Question 15

Provide the structure of (R)-4-ethoxypentanenitrile.

Question 16

Provide the structure of o-bromobenzoyl chloride.

Question 17

Provide the structure of γ-butyrolactam.

Question 18

Provide the proper IUPAC name for the compound below.

Question 19

Cyclic esters are called:

A) lactones.
B) lactams.
C) lacrimals.
D) imides.
E) enamines.

Question 20

Provide the IUPAC name of the following compound.

Question 21

Provide the structure of 3-oxobutanenitrile.

Question 22

Provide the name of the compound shown below.

Question 23

Provide the name of CH₃O₂CH₂CH₂CH₂CH₃.

Question 24

Provide the name of the compound shown below.

Question 25

What is the common name for the following carboxylic acid derivative?

A) β-hydroxybutyronitrile
B) 1-cyano-2-butanol
C) β-hydroxyvaleronitrile
D) γ-hydroxyvaleronitrile
E) 2-hydroxypentane nitrile

Question 26

Provide the structure of N,N-diethylbutanamide.

Question 27

What is the correct IUPAC name for the following compound?

A) N-ethyl-2,N-dimethylbutanamide
B) N-ethyl-N-methylisobutyramide
C) 2,N-dimethyl-N-ethylbutanamide
D) 1-(ethylmethylamino)-2-methylbutanamide

Question 28

Provide the IUPAC name for HCONHCH₂CH₂CH₃.

Question 29

Arrange the following compounds in order of increasing boiling point: acetic acid, propanenitrile, butane, and acetamide.

Question 30

List the following five compounds, ethanamide, 1-propanol, methyl formate, acetic acid, and propanenitrile, in order of increasing boiling point. Start with the lowest boiling compound.

Question 31

Arrange the following three amides in order of increasing boiling point: propanamide, N-methylacetamide, and N,N-dimethylformamide.

Question 32

In ¹H NMR, the chemical shifts for protons α to a carbonyl group:

A) are similar for all acid derivatives.
B) are farthest downfield for carboxylic acids.
C) are farther downfield than those α to a nitrile.
D) fall between δ 3.1 and δ 4.2 (ppm).
E) fall between δ 1.3 and δ 1.8 (ppm).

Question 33

While the carbonyl stretching frequency for simple aldehydes, ketones, and carboxylic acids is about 1710 cm^-1, the carbonyl stretching frequency for acid chlorides is about ________.

A) 1700 cm^-1
B) 1735 cm^-1
C) 1800 cm^-1
D) 1660 cm^-1
E) 2200 cm^-1

Question 34

In the proton NMR spectrum of a secondary amide, the amide proton's signal is:

A) sharp, around δ 5.0 (ppm).
B) sharp, around δ 10.0 (ppm).
C) broad, around δ 9.0 (ppm).
D) broad, around δ 7.0 (ppm).
E) usually not observed.

Question 35

Provide the proper IUPAC name for NCCH₂CH₂CH₂CH₂CO₂CH₃.

Question 36

Identify the correct IUPAC systematic name for the structure below.

A) N-methyl-2-ethyl-5-methyloctanamide
B) 6,N-dimethylnonane-3-carboxamide
C) 5,N-dimethyl-2-ethyloctanamide
D) 2-ethyl-5,N-dimethyloctanamide

Question 37

While the carbonyl stretching frequency for simple aldeydes, ketones, and carboxylic acids is about 1710 cm^-1, the carbonyl stretching frequency for esters is about ________.

A) 1660 cm^-1
B) 1700 cm^-1
C) 1735 cm^-1
D) 1800 cm^-1
E) 2200 cm^-1

Question 38

Provide the structure of 2-bromo-2-methylbutanoyl chloride.

Question 39

While the carbonyl stretching frequency for simple aldehydes, ketones, and carboxylic acids is about 1710 cm^-1, the carbonyl stretching frequency for amides is about ________.

A) 1700 cm^-1
B) 1735 cm^-1
C) 1800 cm^-1
D) 1660 cm^-1
E) 2200 cm^-1

Question 40

Which of the following are strongly hydrogen bonded in the liquid phase?

A) nitriles
B) esters
C) secondary amides
D) tertiary amides
E) acid chlorides

Question 41

A correct order of reactivity of acid derivatives towards nucleophilic attack is:

A) esters > acid anhydrides > amides.
B) anhydrides > amides > esters.
C) carboxylates > esters > amides.
D) anhydrides > acids > acid chlorides.
E) anhydrides > amides > carboxylates.

Question 42

The following compound is a tumor growth inhibitor (J. Med. Chem. 2011, 1789). Circle all carbon centers that are at the same oxidation state as a carboxylic acid.

Question 43

What compound results when ethyl benzoate is stirred in methanol containing a trace of HCl and by what name is this process known?

Question 44

Name the compound which results when δ-valerolactone is heated in a large excess of methanol in the presence of catalytic acid.

Question 45

Which compound has a carbonyl stretch in its IR spectrum at the lowest wavenumber?

A) acetic anhydride
B) formamide
C) cyclohexanone
D) propanoyl chloride
E) ethyl acetate

Question 46

The most characteristic IR stretch of butanenitrile occurs at approximately what wavenumber?

A) 3500 cm^-1
B) 3100 cm^-1
C) 2600 cm^-1
D) 2200 cm^-1
E) 1750 cm^-1

Question 47

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

Question 48

Using the two key resonance structures for an ester, show how resonance stabilization is lost when an ester is attacked by a nucleophile.

Question 49

Which of the following is the most reactive carboxylic acid derivative?

A) ester
B) anhydride
C) nitrile
D) acid chloride
E) amide

Question 50

Using potential energy diagrams, explain why alkoxides act as leaving groups in nucleophilic acyl substitutions but not in S_N2 reactions.

Question 51

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

Question 52

Which of the following reactions is favorable, in the direction indicated, under fairly "normal" laboratory conditions?

A)

B)

C)

D)

E)

Question 53

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 54

Name the compound which results when propyl benzoate is heated in a large excess of ethanol in the presence of catalytic acid.

Question 55

Predict the major product of the following reaction.

Question 56

Arrange the carboxylic acid derivatives below in order of increasing reactivity towards nucleophilic acyl substitution.

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

Question 57

Provide an arrow pushing mechanism for the following reaction. Show all
intermediate structures and formal charges. You do not need to show resonance structures.

Question 58

List the following four carboxylic acid derivatives, ester, anhydride, amide, and acid halide, in order of increasing reactivity in nucleophilic acyl substitution reactions. Start with the least reactive derivative.

Question 59

Describe, in short phrases, the three step mechanism by which hexanoyl chloride reacts with dimethylamine.

Question 60

Draw the product resulting from the following reaction. Indicate any relevant stereochemistry.

Question 61

Distamycin and derivatives have exhibited antiviral, antibiotic, and antitumor activity by binding to the minor groove of DNA (J. Med. Chem. 2004, 2133). Place a line through each bond of distamycin that would be cleaved by acid hydrolysis.

Question 62

Which of the following compounds is(are) hydrolyzed to butanoic acid upon heating in H₂O, H₂SO₄?

A) ethyl butanoate
B) butyl acetate
C) N-methylbutanamide
D) both A and B
E) both A and C

Question 63

Acids can be converted to primary amines by:

A) conversion to the nitrile followed by treatment with LiAlH₄.
B) conversion to the diazonium salt followed by treatment with NaBH₄.
C) conversion to the primary amide followed by treatment with LiAlH₄.
D) both A and B.
E) both A and C.

Question 64

Acids can be reduced to aldehydes by:

A) treatment with LiAlH₄.
B) conversion to the acid chloride followed by treatment with LiAlH[OC(CH₃)₃]₃.
C) conversion to the amide followed by treatment with NaBH₄.
D) conversion to the ester followed by treatment with LiAlH₄.
E) conversion to the anhydride followed by treatment with Mg and H₃O⁺.

Question 65

Provide the major organic product in the reaction shown below.

Question 66

Which sequence ranks the following carboxylic acid derivatives in order of increasing rate of hydrolysis?

A) 2 < 3 < 1
B) 3 < 2 < 1
C) 2 < 1 < 3
D) 1 < 3 < 2

Question 67

Lithium aluminum hydride reduces carboxylic acids, acid chlorides, and esters to:

A) aldehydes.
B) primary alcohols.
C) secondary alcohols.
D) tertiary alcohols.
E) ketones.

Question 68

Provide the major organic product in the reaction shown below.

Question 69

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 70

Which of the following are intermediates in the acid hydrolysis of an amide?

A) 1
B) 2
C) 2 & 3
D) 4
E) 1, 2, & 3

Question 71

What compound is produced when N,N-dimethylpropanamide is treated with LiAlH₄?

A) CH₃CH₂CONH₂
B) CH₃CH₂CH₂NH₂
C) CH₃CH₂CH₂OH
D) CH₃CH₂CH₂N(CH₃)₂
E) CH₃CH₂N(CH₃)₂

Question 72

Which sequence correctly lists the following structures in order of increasing rate of hydrolysis to a carboxylic acid under basic conditions?

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

Question 73

Typically, amides will hydrolyze under ________ conditions than esters.

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

Question 74

Predict the major product of the following reaction.

Question 75

Predict the major product of the following reaction.

Question 76

Two equivalents of methyl magnesium bromide will add to:

A) lactones.
B) aldehydes.
C) ketones.
D) imines.
E) secondary amines.

Question 77

Predict the major product of the following reaction.

Question 78

The hydrolysis of esters, amides, and nitriles:

A) can be carried out under acidic or basic conditions.
B) must be acid-catalyzed.
C) must be base-catalyzed.
D) should be carried out at pH 7.0 for optimum efficiency.
E) is not pH dependent.

Question 79

Provide the major organic product in the reaction of CH₃CH₂CONH₂ with hot aqueous acid.

Question 80

Predict the major product of the following reaction.