Deck 18: Functional Derivatives of Carboxylic Acids

Question 1

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

Answer 1

addition followed by elimination

Question 2

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

Answer 2

1 = benzonitrile; 2 = benzamide; 3 = benzoic acid

Question 3

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

Answer 3

addition followed by elimination

Question 4

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

Question 5

What is the IUPAC name of the following compound?

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

Question 6

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 7

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 8

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

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

Question 9

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

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

Question 10

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 11

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 12

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 13

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 14

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 15

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 16

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 17

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 18

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 19

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 20

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

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 obtained from the following reaction?

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

Question 44

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

A) 1. LiAlH₄; 2. H₃O⁺
B) 1. 2 eq. CH₃MgBr; 2. H₃O⁺
C) 1. (CH₃)₂CuLi; 2. H₃O⁺
D) 1. 2 eq. CH₃I

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 major organic product obtained from the following reaction?

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

Question 47

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

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

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 best choice of reagent to achieve the following transformation?

A) CH₃MgBr
B) CH₃Li
C) CH₃I
D) (CH₃)₂CuLi

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 of the following sequence of reactions?

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 obtained from the following reaction?

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

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

Question 61

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

Question 62

What two organic compounds are obtained from the following reaction?

Question 63

What two organic compounds are obtained from the following reaction?

Question 64

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

Question 65

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

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

Question 66

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

Question 67

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

Question 68

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 69

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 70

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 71

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

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

Question 72

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

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

Question 73

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

Question 74

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

Question 75

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

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

Question 76

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 77

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

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

Question 78

What two organic compounds are obtained from the following reaction?

Question 79

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

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

Question 80

What two organic compounds are obtained from the following reaction?