Deck 17: Carboxylic Acids and Their Derivatives

Question 1

A correct name for is:

A)2-Methylbutyl 2-methylbutanoate
B)2-Methylbutyl 3-methylbutanoate
C)3-Methylbutyl isovalerate
D)Isopentyl isovalerate
E)Isopentyl isobutyrate

Answer 1

2-Methylbutyl 3-methylbutanoate

Question 2

The correct structure for 2-methylbutyl methanoate is:

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

Answer 2

III

Question 3

The correct structure for methyl bicyclo[2.2.2]octane-1-carboxylate is:

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

Answer 3

IV

Question 4

What is the IUPAC name for

A)"2,3-Dimethylbutyl acetate-"
B)"2,3-Dimethyl-4-oxoethanal"
C)"2,3-Dimethylbutyl methanoate"
D)"2,3-Dimethylbutyl methylate"
E)"2,3-Dimethylbutyl formylate"

Question 5

The correct structure for methyl bicyclo[2.2.2]octane-2-carboxylate is:

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

Question 6

Which compound would be the strongest acid?

A)4,4-dichlorobutanoic acid
B)3,4-dichlorobutanoic acid
C)3,3-dichlorobutanoic acid
D)2,3-dichlorobutanoic acid
E)2,2-dichlorobutanoic acid

Question 7

Which of the following is the best name for the following compound?

A)Isobutyl ethanoate
B)Ethyl isopropanoate
C)3-methylbutyl ethanoate
D)Ethoxy isobutyl ketone
E)Ethyl 3-methylbutanoate

Question 8

The correct structure for bicyclo[1.1.1]pentane-2-carboxylic acid is:

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

Question 9

What is the IUPAC name for

A)" $\infty$ -Chlorovaleryl chloride"
B)"2-Chloropentanoyl chloride"
C)"1-Chloropentanoyl chloride"
D)"1,2-Dichloropentanal"
E)"1-Chloro-1-butanecarbonyl chloride"

Question 10

The correct structure for bicyclo[2.2.2]octane-2-carboxylic acid is:

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

Question 11

The correct structure for ethyl 3-methylbutanoate is:

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

Question 12

Which of the following structures is 3,4-dimethylpentyl chloroformate?

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

Question 13

The correct structure for bicyclo[1.1.0]butane-2-carboxylic acid is:

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

Question 14

The correct structure for ethyl 3-methylbutanoate is:

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

Question 15

The correct structure for ethyl 2-chloropentanoyl chloride is:

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

Question 16

Which compound would be the weakest acid?

A)CHCl₂CH₂CH₂CO₂H
B)ClCH₂CHClCH₂CO₂H
C)CH₃CCl₂CH₂CO₂H
D)CH₃CHClCHClCO₂H
E)CH₃CH₂CCl₂CO₂H

Question 17

Which of the following structures is N-benzyl-N-propyl-2,3-dimethylbutanamide?

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

Question 18

Which compound would be the strongest acid?

A)CHCl₂CH₂CH₂CO₂H
B)ClCH₂CHClCH₂CO₂H
C)CH₃CCl₂CH₂CO₂H
D)CH₃CHClCHClCO₂H
E)CH₃CH₂CCl₂CO₂H

Question 19

The correct structure for methyl bicyclo[1.1.0]butane-2-carboxylate is:

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

Question 20

The correct structure for methyl bicyclo[1.1.1]pentane-2-carboxylate is:

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

Question 21

Which of the following would be the strongest acid?

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

Question 22

In which of the following sequences are the compounds listed in order of decreasing acidity?

A)CH₃COOH > H₂O > CH₃CH₂OH > HC $\equiv$ CH > NH₃
B)CH₃CH₂OH > CH₃COOH > H₂O > HC $\equiv$ CH > NH₃
C)CH₃COOH > CH₃CH₂OH > H₂O > NH₃ > HC $\equiv$ CH
D)H₂O > CH₃COOH > CH₃CH₂OH > HC $\equiv$ CH > NH₃
E)CH₃CH₂OH > H₂O > CH₃COOH > HC $\equiv$ CH > NH₃

Question 23

Which of the following would be the weakest acid?

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

Question 24

Which compound would be expected to have the highest pK_a?

A)4,4-dichlorobutanoic acid
B)3,4-dichlorobutanoic acid
C)3,3-dichlorobutanoic acid
D)2,3-dichlorobutanoic acid
E)2,2-dichlorobutanoic acid

Question 25

Which compound would be the weakest acid?

A)water
B)acetic acid
C)ethane
D)acetylene
E)ethanol

Question 26

Which compound would be the strongest acid?

A)water
B)acetic acid
C)ethane
D)acetylene
E)ethanol

Question 27

Which compound would be expected to have the lowest pK_a?

A)water
B)acetic acid
C)ethane
D)acetylene
E)ethanol

Question 28

Which of the following would be the strongest acid?

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

Question 29

Which of the following would be the weakest acid?

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

Question 30

In which of the following sequences are the compounds listed in order of decreasing acidity?

A)PhCOOH > H₂O > PhOH > PhCH₂OH > PhH
B)PhCOOH > PhOH > H₂O > PhCH₂OH > PhH
C)PhH > H₂O > PhOH > PhCH₂OH > PhCOOH
D)PhOH > H₂O > PhCOOH > PhCH₂OH > PhH
E)PhCOOH > H₂O > PhOH > PhH > PhCH₂OH

Question 31

Which compound would be the weakest acid?

A)4,4-dichlorobutanoic acid
B)3,4-dichlorobutanoic acid
C)3,3-dichlorobutanoic acid
D)2,3-dichlorobutanoic acid
E)2,2-dichlorobutanoic acid

Question 32

Which compound would be expected to have the lowest pK_a?

A)4,4-dichlorobutanoic acid
B)3,4-dichlorobutanoic acid
C)3,3-dichlorobutanoic acid
D)2,3-dichlorobutanoic acid
E)2,2-dichlorobutanoic acid

Question 33

Which of the following would be the strongest acid?

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

Question 34

Which of the following would be the strongest acid?

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

Question 35

Which of the following would be the weakest acid?

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

Question 36

Which of the following would be the strongest acid?

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

Question 37

Which compound would be expected to have the highest pK_a?

A)water
B)acetic acid
C)ethane
D)acetylene
E)ethanol

Question 38

Which of the following would be the strongest acid?

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

Question 39

In which of the following sequences are the compounds listed in order of decreasing acidity?

A)CH₃COOH > H₂O > PhOH > HC $\equiv$ CH > NH₃
B)PhOH > CH₃COOH > H₂O > HC $\equiv$ CH > NH₃
C)CH₃COOH > PhOH > H₂O > HC $\equiv$ CH > NH₃
D)H₂O > CH₃COOH > PhOH > HC $\equiv$ CH > NH₃
E)PhOH > H₂O > CH₃COOH > HC $\equiv$ CH > NH₃

Question 40

In which of the following sequences are the compounds listed in order of increasing acidity?

A)NH₃ < HC $\equiv$ CH < CH₃CH₂OH < H₂O < CH₃COOH
B)CH₃CH₂OH < NH₃ < H₂O < HC $\equiv$ CH < CH₃COOH
C)CH₃COOH < CH₃CH₂OH < H₂O < NH₃ < HC $\equiv$ CH
D)H₂O < CH₃COOH < CH₃CH₂OH < HC $\equiv$ CH < NH₃
E)NH₃ < H₂O < CH₃COOH < HC $\equiv$ CH < CH₃CH₂OH

Question 41

Which of the following acids would be expected to have the largest value for pK_a?

A)4-bromobutanoic acid
B)4-chlorobutanoic acid
C)4,4-dichlorobutanoic acid
D)4-bromo-4-iodobutanoic acid
E)4-bromo-4,4-dichlorobutanoic acid

Question 42

Which of the following acids would be expected to have the smallest value for pK_a?

A)Acetic acid
B)Ethanol
C)Phenol
D)Acetone
E)Water

Question 43

In which of the following are the compounds listed in order of decreasing acidity?

A)CH₃CO₂H > CH₃CH₂OH > C₆H₅OH > H₂O
B)C₆H₅OH > CH₃CO₂H > H₂O > CH₃CH₂OH
C)CH₃CO₂H > H₂O > C₆H₅OH > CH₃CH₂OH
D)H₂O > CH₃CO₂H > C₆H₅OH > CH₃CH₂OH
E)None of these choices.

Question 44

Which of the following acids would have the smallest value for pK_a1?

A)HOOCCH₂CH₂CH₂CH₂CH₂COOH
B)HOOCCH₂CH₂CH₂CH₂COOH
C)HOOCCH₂CH₂CH₂COOH
D)HOOCCH₂CH₂COOH
E)HOOCCH₂COOH

Question 45

A compound has the molecular formula,C₆H₁₂O₂.Its IR spectrum shows a strong absorption band near 1740 cm^-1; its ¹H NMR spectrum consists of two singlets,at $\delta$ 1.4 and $\delta$ 2.0.The most likely structure for this compound is:

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

Question 46

Which compound would be most acidic?

A)
B)
C)
D)
E)

Question 47

Which of the following would be the strongest acid?

A)2,3-Dimethylhexanoic acid
B)3,3-Diiodopentanoic acid
C)3-Iodo-4-bromopentanoic acid
D)3-Chloro-4-bromohexanoic acid
E)2-Fluoro-4-bromopentanoic acid

Question 48

A compound has the molecular formula C₈H₁₄O₄.Its IR spectrum shows a strong absorption band near 1740 cm^-1.Its ¹H NMR spectrum consists of: triplet, $\delta$ 1.3
Singlet, $\delta$ 2.6
Quartet, $\delta$ 4.2
The most likely structure for the compound is:

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

Question 49

Which of the following would be the weakest acid?

A)Benzoic acid
B)4-Nitrobenzoic acid
C)4-Methylbenzoic acid
D)4-Methoxybenzoic acid
E)4-Iodobenzoic acid

Question 50

Which of the following acids would have the smallest value for pK_a?

A)BrCH₂CH₂CH₂COOH
B)ClCH₂CH₂CH₂COOH
C)Cl₂CHCH₂CH₂COOH
D)ICHBrCH₂CH₂COOH
E)BrCCl₂CH₂CH₂COOH

Question 51

A compound has the molecular formula,C₆H₁₂O₂.Its IR spectrum shows a strong absorption band near 1740 cm^-1; its ¹H NMR spectrum consists of two singlets,at $\delta$ 1.2 and $\delta$ 3.6.The most likely structure for this compound is:

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

Question 52

Which of the following acids would be expected to have the smallest value for pK_a?

A)2,3-Dimethylhexanoic acid
B)3,3-Diiodopentanoic acid
C)3-Iodo-4-bromopentanoic acid
D)3-Chloro-4-bromohexanoic acid
E)2-Fluoro-4-bromopentanoic acid

Question 53

The IR spectrum of a compound exhibits a broad absorption band at 2500-3000 cm^-1 and a sharp band at 1710 cm^-1.Which of these compounds could it be?

A)1-Butanol
B)Propyl acetate
C)Butanoic acid
D)Acetyl chloride
E)Acetic anhydride

Question 54

Which compound would be most acidic?

A)Acetic acid
B)Ethanol
C)Phenol
D)Acetone
E)Water

Question 55

Which of the following acids would have the largest value for pK_a?

A)BrCH₂CH₂CH₂COOH
B)ClCH₂CH₂CH₂COOH
C)Cl₂CHCH₂CH₂COOH
D)ICHBrCH₂CH₂COOH
E)BrCCl₂CH₂CH₂COOH

Question 56

Which of the following acids would be expected to have the smallest value for pK_a?

A)Benzoic acid
B)4-Nitrobenzoic acid
C)4-Methylbenzoic acid
D)4-Methoxybenzoic acid
E)4-Iodobenzoic acid

Question 57

Which of the following acids would be expected to have the largest value for pK_a?

A)Benzoic acid
B)4-Nitrobenzoic acid
C)4-Methylbenzoic acid
D)4-Methoxybenzoic acid
E)4-Iodobenzoic acid

Question 58

Which of the following acids would be expected to have the smallest value for pK_a?

A)4-bromobutanoic acid
B)4-chlorobutanoic acid
C)4,4-dichlorobutanoic acid
D)4-bromo-4-iodobutanoic acid
E)4-bromo-4,4-dichlorobutanoic acid

Question 59

Which of the following would be the strongest acid?

A)Benzoic acid
B)4-Nitrobenzoic acid
C)4-Methylbenzoic acid
D)4-Methoxybenzoic acid
E)4-Iodobenzoic acid

Question 60

In which of the following are the compounds listed in order of decreasing acidity?

A)CH₃CO₂H > CH₃CH₂OH > C₆H₅OH > H₂O
B)C₆H₅OH > CH₃CO₂H > H₂O > CH₃CH₂OH
C)CH₃CO₂H > H₂O > C₆H₅OH > CH₃CH₂OH
D)H₂O > CH₃CO₂H > C₆H₅OH > CH₃CH₂OH
E)CH₃CO₂H > C₆H₅OH > CH₃CH₂OH > H₂O

Question 61

What would be the product of the following reaction? \

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

Question 62

What is the expected product,A,of the following reaction sequence?

A)HCO₂CH₂C₆H₅
B)C₆H₅CH₂COOH
C)C₆H₅CH₂OSO₃H
D)C₆H₅CHClCOOH
E)O=C(CH₂C₆H₅)₂

Question 63

What would be the final organic product of the following reaction?

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

Question 64

What would be the final organic product of the following reaction?

A)(CH₃)₃CCO₂H
B)(CH₃)₃CCOCH₃
C)(CH₃)₃CCH₂OH
D)(CH₃)₃COCH₃
E)(CH₃)₃CCO₂CH₃

Question 65

What would be the final organic product of the following reaction?

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

Question 66

What is the expected product,A,of the following reaction sequence?

A)HCO₂CH₂C₆H₅
B)C₆H₅CH₂COOH
C)C₆H₅CH₂OSO₃H
D)C₆H₅CHClCOOH
E)O=C(CH₂C₆H₅)₂

Question 67

Predict the major organic product of the reaction sequence,

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

Question 68

Predict the major organic product of the reaction sequence,

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

Question 69

Predict the major organic product of the reaction sequence,

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

Question 70

A compound with the molecular formula C₁₈H₁₈O₄ has a ¹H NMR spectrum that consists of: singlet, $\delta$ 2.7
Singlet, $\delta$ 3.1
Multiplet, $\delta$ 7.3
The IR spectrum shows a strong absorption band near 1750 cm^-1.The most likely structure for the compound is:

A)
B)
C)
D)
E)

Question 71

What would be the final organic product of the following reaction?

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

Question 72

What is the product of this reaction?

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

Question 73

What is the reactant of the following reaction sequence?

A)HCO₂CH₂C₆H₅
B)C₆H₅CH₂COOH
C)C₆H₅CH₂Cl
D)C₆H₅CHClCOOH
E)O=C(CH₂C₆H₅)₂

Question 74

The product,Z,of the following sequence of reactions is which compound?

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

Question 75

Predict the major organic product of the reaction sequence below:

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

Question 76

What would be the final organic product of the following reaction?

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

Question 77

The product of the following reaction is:

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

Question 78

A compound with the molecular formula C₅H₁₀O₂ gave the following ¹H NMR spectrum: triplet, $\delta$ 0.90
Multiplet, $\delta$ 1.60
Singlet, $\delta$ 1.95
Triplet, $\delta$ 3.95
The IR spectrum showed a strong absorption band near 1740 cm^-1.The most likely structure for the compound is:

A)
B)
C)
D)
E)

Question 79

What is the product of this reaction?

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

Question 80

What would be the final organic product of the following reaction?

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