Deck 16: Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

Question 1

Provide the proper IUPAC name for the compound below.

Answer 1

isopropyl cyclohexanecarboxylate

Question 2

Which of the following compounds is g-butyrolactone?

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

Answer 2

III

Question 3

Which of the following compounds is an amide?

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

Answer 3

III

Question 4

Provide the proper IUPAC name for the compound below.

Question 5

Which of the following compounds is an anhydride?

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

Question 6

What is the common name for the following compound?

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

Question 7

Provide the proper IUPAC name for ClCH₂CH₂CONHCH₃.

Question 8

Which of the following compounds is an acyl chloride?

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

Question 9

Which of the following compounds is benzoyl chloride?

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

Question 10

Which of the following compounds is an ester?

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

Question 11

Provide the structure of propanoic anhydride.

Question 12

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 13

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

Question 14

Which of the following compounds is methyl formate?

A)
B)
C)
D)
E)

Question 15

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

Question 16

Which of the following compounds is D-valerolactam?

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

Question 17

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 18

What is the common name for the following compound?

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

Question 19

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 20

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

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

Question 21

Provide the IUPAC name for the organic compound below.

Question 22

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

Question 23

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 24

Give the systematic name of the structure.

Question 25

Give the name of the structure.

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

Question 26

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 27

Arrange the compounds below in order of increasing boiling point.

Question 28

Give the name of the structure.

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

Question 29

Provide the IUPAC name for the organic compound below.

Question 30

Provide the IUPAC name for the organic compound below.

Question 31

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 32

Provide the name of the compound below.

Question 33

Which of the following compounds has the lowest boiling point?

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

Question 34

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 35

Provide the systematic name of the compound shown below.

Question 36

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 37

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 38

Give the systematic name of the structure.

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

Question 39

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 40

Which of the following statements is not true about fatty acids?

A)Fatty acids are carboxylic acids with long hydrocarbon side chains.
B)The double bonds in unsaturated fatty acids are always conjugated.
C)Most naturally occurring fatty acids contain even numbers of carbons and are unbranched.
D)Fatty acids can be saturated or unsaturated.
E)Physical properties of fatty acids depend on the length of the hydrocarbon chain and the degree of unsaturation.

Question 41

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

A)
B)
C)
D)
E)

Question 42

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

A)
B)
C)
D)
E)

Question 43

Identify the compound that would be formed from the hydrogenation of linolenic acid.

A)palmitic acid
B)lauric acid
C)stearic acid
D)myristic acid
E)linoleic acid

Question 44

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

Question 45

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

A)
B)
C)
D)
E)

Question 46

Which of the following statements is true for both cholesterol and vitamin A?

A)Both are vitamins.
B)Both are proteins.
C)Both are lipids.
D)Both are steroids.
E)Both are fatty acids.

Question 47

In an MO depiction of the carbonyl's reactivity with an amine nucleophile, the most important MO overlap occurs between the amine's lone pair and the carbonyl's ________.

A)π_c-o
B)π*_c-o
C)σ_c-o
D)σ*_c-o
E)n_o

Question 48

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 49

What organic compounds are formed when linoleic acid, CH₃(CH₂)₄CH CHCH₂CH CH(CH₂)₇CO₂H, is ozonolyzed and subsequently treated with H₂O₂?

Question 50

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 51

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

A)
B)
C)
D)
E)

Question 52

Identify the compound with the highest melting point.

A)palmitic acid
B)lauric acid
C)stearic acid
D)myristic acid
E)linoleic acid

Question 53

Which of the following terms best describes the compound below? CH₃(CH₂)₇CH CH(CH₂)₇CO₂H

A)an unsaturated fatty acid
B)a triglyceride
C)a synthetic detergent
D)a micelle
E)isoprene

Question 54

Palmitic acid (hexadecanoic acid)has a melting point of 63°C. Palmitoleic acid (9-hexadecenoic acid)has a melting point of 32°C. Explain this difference in melting points.

Question 55

Why do most naturally occurring fatty acids contain an even number of carbon atoms?

Question 56

Which of the following best explains why the melting points of saturated fats increase with increasing molecular weight?

A)decreased polarity
B)decreased hydrogen bonding
C)increased hydrogen bonding
D)decreased intermolecular van der Waal's interactions
E)increased intermolecular van der Waal's interactions

Question 57

Which of the following terms best describes the compound below? CH₃(CH₂)₁₂CO₂H

A)a fatty acid
B)an oil
C)a wax
D)a soap
E)a phosphatidic acid

Question 58

Myristic acid has the formula CH₃(CH₂)₁₂CO₂H. Provide the structure of the triglyceride trimyristin.

Question 59

Which of the following fatty acids cannot be synthesized by mammals but must be included in the diet because it is needed to synthesize arachidonic acid which in turn will synthesize prostaglandins?

A)Lauric acid
B)Palmitic acid
C)Arachidic acid
D)Linoleic acid
E)Oleic acid

Question 60

Which of the following compounds is hydrolyzed most rapidly inaqueous NaOH?

A)
B)
C)
D)
E)

Question 61

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

A)
B)CH₃C N
C)
D)
E)all the above

Question 62

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 63

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

Question 64

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 65

Provide the major organic product of the following.

Question 66

Which of the following is the best method for preparing

A)
B)
C)
D)
E)

Question 67

Provide the major organic product of the reaction below.

Question 68

Give the product of the reaction.

A)
B)
C)
D)
E)

Question 69

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

Question 70

Provide the major organic product of the following.

Question 71

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

Question 72

Give the product of the reaction.

A)
B)
C)
D)
E)

Question 73

Typically, amides will hydrolyze under ________ conditions than esters.

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

Question 74

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

Question 75

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

Question 76

Provide the major organic product of the reaction below.

Question 77

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 78

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 79

Which of the following is (are)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 80

What are the products from the following reaction?