Deck 18: Functional Derivatives of Carboxylic Acids

Question 1

What is the IUPAC name of the following compound?

A)butyl isopropanoate
B)isopropyl pentanoate
C)pentanoyl isopropane
D)isopropyloxybutanal

Answer 1

isopropyl pentanoate

Question 2

What is the IUPAC name of the following compound?

A)dimethylamino-3-phenylpropanoic acid
B)N,N-dimethyl 2-phenylethyl amide
C)N,N-dimethyl 3-phenylpropanamide
D)dimethyl 2-phenylpropanoylamine

Answer 2

N,N-dimethyl 3-phenylpropanamide

Question 3

What is the correct assignment of the functional groups in the following compounds?

A)1 = amide; 2 = imide; 3 = nitrile
B)1 = lactam; 2 = amide; 3 = imide
C)1 = lactam; 2 = imide; 3 = amide
D)1 = imide; 2 = amide; 3 = lactam

Answer 3

1 = lactam; 2 = amide; 3 = imide

Question 4

What is the correct assignment of the names of the following substituted benzenes?

A)1 = benzonitrile; 2 = benzyl amine; 3 = benzyl alcohol
B)1 = benzyl amine; 2 = benzonitrile; 3 = benzamide
C)1 = benzamide; 2 = benzonitrile; 3 = benzoic acid
D)1 = benzonitrile; 2 = benzamide; 3 = benzoic acid

Question 5

Which of the following best describes the key mechanistic steps in the reaction of an acid chloride and an alcohol to form an ester?

A)elimination followed by addition
B)addition followed by decarboxylation
C)addition followed by elimination
D)substitution followed by addition

Question 6

Which of the following compounds is a 3 ^$\circ$ amide?

A)1
B)2
C)3
D)4

Question 7

Which of the following can be made by acid-promoted hydrolysis of a nitrile?
1)an acid
2)an alcohol
3)an imine
4)an imide

A)only 1
B)only 1 and 2
C)only 2 and 3
D)only 4

Question 8

Which of the following is the correct order of decreasing acid strength of the following compounds (more acidic > less acidic)?

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

Question 9

Which of the following is the correct order of decreasing leaving group ability in nucleophilic acyl substitutions (better leaving group > worse leaving group)?

A)Cl^- > CH₃COO^- > CH₃O^-
B)CH₃COO^- > CH₃O^- > Cl^-
C)Cl^- > CH₃O^- > CH₃COO^-
D)CH₃O^- > Cl^- > CH₃COO^-

Question 10

Which of the following is the correct order of decreasing reactivity in hydrolysis reactions (more reactive > less reactive)?

A)anhydrides > amides > acid chlorides
B)amides > acid chlorides > anhydrides
C)anhydrides > acid chlorides > amides
D)acid chlorides > anhydrides > amides

Question 11

Which of the following is the correct order of decreasing leaving group ability in nucleophilic acyl substitutions (better leaving group > worse leaving group)?

A)Cl^- > NH₂^- > CH₃O^-
B)NH₂^- > CH₃O^- > Cl^-
C)Cl^-> CH₃O^- > NH₂^-
D)CH₃O^- > Cl^- > NH₂^-

Question 12

What of the following is the correct assignment of the classes of the following compounds?

A)1 = lactone; 2 = ester; 3 = amide
B)1 = ester; 2 = ester; 3 = imide
C)1 = ester; 2 = imide; 3 = amide
D)1 = lactone; 2 = anhydride; 3 = imide

Question 13

Which of the following is the correct order of decreasing acid strength of the following compounds (more acidic > less acidic)?

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

Question 14

What is the IUPAC name of the following compound?

A)(E)-N-methyl 3-methyl-3-pentenamide
B)(Z)-N-methyl 3-methyl-3-pentenamide
C)(E)-1-methylamino-3-methyl-3-pentenal
D)(Z)-1-methylamino-3-methyl-3-pentenal

Question 15

What is the correct assignment of the functional groups in the following compounds?

A)1 = amide; 2 = ester; 3 = nitrile
B)1 = nitrile; 2 = ester; 3 = imide
C)1 = nitrile; 2 = ester; 3 = amide
D)1 = amide; 2 = carboxylic acid; 3 = imide

Question 16

Which of the following statements is not true in relation to the hydrolysis of esters?

A)Hydrolysis of esters under acid conditions requires only a catalytic amount of a strong acid
B)Hydrolysis of esters under basic conditions requires a stoichiometric amount of hydroxide
C)Under acidic conditions for hydrolysis of esters protonation of the ester increases its electrophilicity
D)Under basic conditions for hydrolysis of esters deprotonation of the ester increases its nucleophilicity

Question 17

Which of the following is the correct order of decreasing reactivity in hydrolysis reactions (more reactive > less reactive)?

A)esters > amides > acid chlorides
B)amides > acid chlorides > esters
C)acid chlorides > esters > amides
D)esters > acid chlorides > amides

Question 18

Which of the following best describes the key mechanistic steps in the reaction of an anhydride and an amine to form an amide?

A)addition followed by elimination
B)elimination followed by addition
C)substitution followed by addition
D)addition followed by decarboxylation

Question 19

What is the IUPAC name of the following compound?

A)ethyl (R)-3-methylpentanoate
B)ethyl (S)-3-methylpentanoate
C)(R)-2-methylbutyl ethanoate
D)(S)-2-methylbutyl ethanoate

Question 20

Which of the following compounds is a 2 ^$\circ$ amide?

A)1
B)2
C)3
D)4

Question 21

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 22

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 23

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 24

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 25

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 26

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 27

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 28

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 29

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 30

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 31

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 32

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 33

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 34

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 35

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 36

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 37

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 38

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 39

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 40

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 41

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 42

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 43

What is the major organic product of the following sequence of reactions?

A)1
B)2
C)3
D)4

Question 44

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 45

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 46

What is the best choice of reagent(s) to achieve the following transformation?

A)H₂O
B)NaOH, H₂O
C)1. LiAlH₄; 2. H₃O⁺
D)H₂SO₄

Question 47

What is the best choice of reagent to achieve the following transformation?

A)CH₃MgBr
B)CH₃Li
C)CH₃I
D)(CH₃)₂CuLi

Question 48

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 49

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 50

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 51

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 52

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 53

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 54

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 55

What is the major organic product of the following sequence of reactions?

A)1
B)2
C)3
D)4

Question 56

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 57

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 58

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 59

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 60

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 61

Of the following substances, the first and last substance shown are not derivatives of carboxylic acids.

Question 62

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 63

The following compound should be named as cyanopropane.

Question 64

Consider the following reaction. The correct reactant to place in the box is PCl₃.

Question 65

It is possible to directly convert an acid anhydride to an acid chloride.

Question 66

Which combination(s) of organic bromide and carbonyl compound can be used to prepare the following product by reaction of the Grignard reagent derived from the alkyl bromide with the carbonyl compound?

A)only 1
B)only 1 and 2
C)only 1, 2 and 3
D)1, 2, 3 and 4

Question 67

Consider the isotopically tagged substance below. Saponification of this substance will produce the following products.

Question 68

The correct name of the following structure is phenyl benzoate.

Question 69

What is the major organic product obtained from the following reaction?

A)1
B)2
C)3
D)4

Question 70

Which combination(s) of organic bromide and carbonyl compound can be used to prepare the following product by reaction of the Grignard reagent derived from the alkyl bromide with the carbonyl compound?

A)only 1
B)only 1 and 2
C)only 1 and 3
D)only 3 and 4

Question 71

The product of the following reaction would be classified as a carboxylic acid.

Question 72

Consider the following reaction. The structure of the tetrahedral intermediate is

Question 73

What is the major organic product of the following sequence of reactions?

A)1
B)2
C)3
D)4

Question 74

Which combination(s) of alkyl bromide and ester can be used to prepare the following product by reaction of the Grignard reagent derived from the alkyl bromide with the ester?

A)only 1
B)only 2
C)only 1 and 3
D)only 2 and 4

Question 75

What is the major organic product of the following sequence of reactions?

A)1
B)2
C)3
D)4

Question 76

Consider the following reaction. The reactant is a lactam.

Question 77

Both amides and nitriles are acyl derivatives of carboxylic acids.

Question 78

The correct name for the following compound is propyl cyclohexanoate.

Question 79

Which combination(s) of alkyl bromide and ester can be used to prepare the following product by reaction of the Grignard reagent derived from the alkyl bromide with the ester?

A)only 1
B)only 3
C)only 1 and 3
D)only 2 and 4

Question 80

What is the major organic product of the following sequence of reactions?

A)1
B)2
C)3
D)4