Deck 21: Carboxylic Acids and Their Derivatives

Question 1

Provide the structure for 5-chloro-3-isopropyl-octanoic acid

Answer 1

Question 2

Which one of the following compounds is the strongest acid?

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

Answer 2

V

Question 3

What is the common name for the following compound?

A) 3-fluorobutanoic acid
B) 2-fluorobutanoic acid
C) 3-fluorobutyric acid
D)2-fluorobutyric acid
E) none of these

Answer 3

3-fluorobutyric acid

Question 4

Which one of the following compounds has the highest boiling point?

A) butanoic acid
B) 1-butanol
C) 2-butanone
D) methoxyethane
E) butanal

Question 5

Which of the following is the weakest acid?

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

Question 6

Methanoic acid is commonly known as ________.

Question 7

What is the IUPAC name for the following compound?

A)2,4-dimethylheptanedioic acid
B)3,5-dimethylheptanedioic acid
C)2,4-dimethylpentanedioic acid
D)3,5-dimethylpentanedioic acid
E)2,4-dimethylheptanoyl acid

Question 8

What is the IUPAC name for the following compound?

A)2-methylpentanoic acid
B) 3-methylpentanoic acid
C) 2-methylhexanoic acid
D) 3-methylhexanoic acid
E) None of these

Question 9

What is the IUPAC name for the following compound?

Question 10

Provide the structure for (3S,4S)-3-hydroxy-4-phenylnonanoic acid.

Question 11

What is the correct structure for succinic acid

A)I
B)II
C)III
D)IV
E) none of these

Question 12

What is the IUPAC name for the following compound?

Question 13

Which of the following is the strongest acid?

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

Question 14

Ethanoic acid is commonly known as ________.

Question 15

What is the IUPAC name for the following compound?

Question 16

Which one of the following compounds has the highest boiling point?

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

Question 17

Which one of the following is the weakest acid?

A) benzoic acid
B) 4-nitrobenzoic acid
C) 4-ethylbenzoic acid
D) 4-chlorobenzoic acid
E) 4-hydroxybenzoic acid

Question 18

What is the correct structure for trichloroacetic acid?

A)I
B)II
C)III
D)IV
E) none of these

Question 19

Which one of the following is the strongest acid?

A) benzoic acid
B) 4-nitrobenzoic acid
C) 4-ethylbenzoic acid
D) 4-chlorobenzoic acid
E) 4-hydroxybenzoic acid

Question 20

What is the IUPAC name for the following compound?

Question 21

What is the IUPAC name for the following compound?

A) $\gamma$ -methylvaleryl chloride
B) 2-methylpentanoyl chloride
C) 3-methylhexanoyl chloride
D) 3-methylpentanoyl chloride
E) none of these

Question 22

Predict the product for the following reaction.

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

Question 23

Predict the product for the following reaction sequence.

A) I
B) II
C) III
D) IV
E) none of these

Question 24

Predict the product for the following reaction.

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

Question 25

Provide the reagents necessary to carry out the following conversion.

Question 26

Predict the product for the following reaction.

Question 27

Predict the product for the following reaction.

Question 28

Which of the following reagent(s) can be used to carryout the following conversion?

A) PCC/CH₂Cl₂
B) CO₂ followed by H₃O⁺
C) mCPBA
D) Na₂Cr₂O₇/H₂SO₄/H₂O
E) both A & D

Question 29

Predict the product for the following reaction.

A) 3-methyl-2-pentanone
B) 3-methyl -1-propanol
C) 2-methyl-1-butanol
D) 3-methyl-2-pentanol
E) none of these

Question 30

Rank the following acids in decreasing (strongest to weakest) order of acidity.
Explain your choice.

Question 31

Provide the reagents necessary to carry out the following conversion.

Question 32

Provide the reagents necessary to carry out the following conversion.

Question 33

Predict the product for the following reaction sequence.

A) 2,2-dimethylpropanoic acid
B) 3,3-dimethyl-2-butanone
C) 2,2-dimethyl-1-propanol
D) 2,2-dimethylbutanoic acid
E) none of these

Question 34

Provide the reagents necessary to carry out the following conversion.

Question 35

Which one of the following is the strongest acid? Explain your choice. I.

Question 36

Rank the following acids in decreasing (strongest to weakest) order of acidity.

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

Question 37

Predict the product for the following reaction.

Question 38

Which one of the following is the strongest acid?

A) 2,3-dimethylheptanoic acid
B) 3,3-dichlorohexanoic acid
C) 4-bromo-3-iodohexanoic acid
D) 4-bromo-3-chloroheptanoic acid
E) 4-bromo-2-fluorohexanoic acid

Question 39

Predict the product for the following reaction.

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

Question 40

Provide the reagents necessary to carry out the following conversion.

Question 41

Provide the structure for benzoyl chloride.

Question 42

What is the IUPAC name for the following compound?

Question 43

What is the IUPAC name for the following compound?

A) methanoic anhydride
B) ethanoic anhydride
C) acetic anhydride
D) both B & C
E) none of these

Question 44

Provide the structure for 4-ethylbenzoyl chloride

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

Question 45

What is the IUPAC name for the following compound?

A) 2-methylbutyl 3-methylbutanoate
B) 3-methylbutyl 3-methylbutanoate
C) 2-methylbutyl isovalerate
D) 2-methylbutyl 2-methylbutanoate
E) none of these

Question 46

What is the IUPAC name for the following compound?

A)2-methylbutyl acetate
B)3-methylbutyl acetate
C)2-methylbutyl methanoate
D)3-methylbutyl methanoate
E) 3-methylbutyl formate

Question 47

What is the IUPAC name for the following compound?

Question 48

Provide the structure for cyclopentanecarbonyl chloride.

Question 49

Provide the structure for N-methylcyclohexanecarboxamide.

Question 50

Provide the structure for benzyl propionate.

Question 51

What is the IUPAC name for the following compound?

Question 52

What is the IUPAC name for the following compound?

A) methanoic propanoic anhydride
B) methanoic butanoic anhydride
C) ethanoic propionic anhydride
D) ethanoic butanoic anhydride
E) butanoic ethanoic anhydride

Question 53

What is the IUPAC name for the following compound?

A)3-ethyl-2,4-dimethylpentanoyl chloride
B)4-ethyl-3,5-dimethylpentanoyl chloride
C)3-ethyl-2,4-dimethylhexanoyl chloride
D)4-ethyl-3,5-dimethylhexanoyl chloride
E) none of these

Question 54

What is the IUPAC name for the following compound?

A) 2,3-dimethylbutanenitrile
B) $\alpha$ , $\beta$ -dimethylbutyrnitrile
C) $\beta$ , $\gamma$ -dimethylbutyrnitrile
D) 3,4-dimethylbutanenitrile
E) 3,4-dimethylpentanenitrile

Question 55

Provide the structure for N-phenyl-N-propyl-2,3-dimethylbutanamide?

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

Question 56

Provide the structure for acetic formic anhydride.

Question 57

What is the common name for the following compound?

Question 58

What is the IUPAC name for the following compound?

A) sec-butyl ethanoate
B) ethyl 3-methylpentanoate
C) 3-methylbutyl ethanoate
D) ethyl 3-methylbutanoate
E) none of these

Question 59

Provide the structure for benzoic ethanoic anhydride.

Question 60

What is the IUPAC name for the following compound?

A) propanoic anhydride
B) butanoic anhydride
C) propionic anhydride
D) pentanoic anhydride
E) both A & C

Question 61

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) none of these

Question 62

Predict the product for the following reaction.

Question 63

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) none of these

Question 64

Predict the product for the following reaction.

Question 65

Which of the following reactions would not yield isopropyl acetate as major product?

A)


B)


C)

D)

E) A & C

Question 66

Provide the reagents necessary to carry out the following conversion.

Question 67

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) none of these

Question 68

Provide the reagents necessary to convert 4,5-dimethyl-1-hexanol into N-cyclopentyl-4,5-dimethylhexanamide

Question 69

Predict the product for the following reaction.

Question 70

Rank the following carboxylic acid derivatives in decreasing order (most to least) of reactivity towards nucleophilic substitution.

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

Question 71

What is the IUPAC name for the following compound?

Question 72

Provide the reagents necessary to carry out the following conversion.

Question 73

Provide a stepwise synthesis for the following compound using benzyl alcohol as your only source of carbon and using any other reagents necessary.

Question 74

Predict the product for the following reaction.

Question 75

Predict the product for the following reaction.

Question 76

Predict the product for the following reaction.

A) ethyl 3-methylbutanoate
B) ethyl 2-methylpropanoate
C) isobutyl ethanoate
D) 5-methyl-3-hexanone
E) none of these

Question 77

Predict the product for the following reaction.

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

Question 78

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) none of these

Question 79

Provide the structure for 3-ethylbenzonitrile.

Question 80

Rank the following carboxylic acid derivatives in decreasing order (most to least) of reactivity towards nucleophilic substitution.

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