Deck 21: Carboxylic Acid Derivatives

Question 1

Provide the IUPAC name of the following compound.

Answer 1

N-ethyl-N-methylpentanamide

Question 2

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

Answer 2

a secondary amide

Question 3

Provide the structure of γ-butyrolactam.

Answer 3

Question 4

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

Question 5

Provide the structure of propanoic anhydride.

Question 6

Which of the following structures are carboxylic acid derivatives?

Question 7

Provide the proper IUPAC name for the compound below.

Question 8

Provide the proper IUPAC name for ClCH₂CH₂CONHCH₃.

Question 9

Cyclic amides are called ________.

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

Question 10

Provide the proper IUPAC name for the compound below.

Question 11

Cyclic esters are called ________.

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

Question 12

Provide the structure of cyclohexyl formate.

Question 13

Provide the structure of trifluoroacetic anhydride.

Question 14

Provide the IUPAC name of the following compound.

Question 15

Provide the proper IUPAC name for the compound below.

Question 16

Polycaprolactone (shown below) is a biodegradable polymer that can be synthesized from a lactone. Suggest a lactone monomer that could be used to make this polymer.
-[OCO(CH₂)₅-]_n-

Question 17

Provide the name of the compound shown below.

Question 18

Provide the name of the compound shown below.

Question 19

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 20

Provide the structure of o-bromobenzoyl chloride.

Question 21

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 22

How could you tell the two compounds apart using IR spectroscopy?

Question 23

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 24

Provide the name of the compound shown below.

Question 25

Provide the structure of N,N-diethylbutanamide.

Question 26

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 27

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 28

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 29

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

Question 30

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

Question 31

Provide the proper IUPAC name for NCCH₂CH₂CH₂CH₂CO₂CH₃.

Question 32

Provide the name of CH₃O₂CH₂CH₂CH₂CH₃.

Question 33

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 34

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

Question 35

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 36

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 37

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 38

Provide the IUPAC name for HCONHCH₂CH₂CH₃.

Question 39

Provide the structure of 3-oxobutanenitrile.

Question 40

Provide the name of the compound shown below.

Question 41

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

Question 42

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

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

Question 43

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

Question 44

Using ¹H NMR, how would you tell the two esters apart?

Question 45

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

Question 46

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

Question 47

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 48

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 49

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 50

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 51

Explain why alkoxides act as leaving groups in nucleophilic acyl substitutions but not in S_N2 reactions.

Question 52

Explain while this reaction won't proceed as it is written in the forward direction.

Question 53

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

Question 54

Shown below is the structure of Lactimidomycin, a potent inhibitor of cell migration, proliferation and protein synthesis. Identify the carboxylic acid derivative/s in the structure of Lactimidomycin.

A) Ester
B) Anhydride
C) Nitrile
D) Imine

Question 55

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

Question 56

Predict the major product of the following reaction.

Question 57

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 58

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

A)
B)
C)
D)
E)

Question 59

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 60

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

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 are intermediates in the acid hydrolysis of an amide?

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

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

Typically, amides will hydrolyze under ________ conditions than esters.

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

Question 66

Two equivalents of methyl magnesium bromide will add to ________.

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

Question 67

Provide the major organic product in the reaction shown below.

Question 68

Predict the major product of the following reaction.

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

Predict the major product of the following reaction.

Question 71

Predict the major product of the following reaction.

Question 72

Provide the major organic product in the reaction shown below.

Question 73

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

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

Question 74

Predict the major product of the following reaction.

Question 75

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 76

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 77

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

Question 78

Predict the major organic product in the following reaction.

Question 79

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 80

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

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