Deck 21: Carboxylic Acids and Their Derivatives

Question 1

What is the IUPAC name for the following compound?

Answer 1

(3E)-5-ethyl-3-methyl-3-heptenoic acid

Question 2

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

Answer 2

2-methylbutyl-3-methylbutanoate

Question 3

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

Answer 3

Question 4

What is the IUPAC name for the following compound?

Question 5

What is the common name for the following compound?

A) $\gamma$ -fluorobutanoic acid
B) β-fluorobutanoic acid
C) β-fluorobutyric acid
D) $\delta$ -fluorobutyric acid
E)3-fluorobutyric acid

Question 6

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

A)2,3-dimethylheptanoic acid
B)3,3-dichlorohexanoic acid
C)3-iodo-4-bromo-hexanoic acid
D)3-chloro-4-bromoheptanoic acid
E)2-fluoro-4-bromohexanoic acid

Question 7

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

Question 8

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

Question 9

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 10

What is the correct structure for trichloroacetic acid?

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

Question 11

Predict the product for the following reaction.

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

Question 12

What is the correct structure for succinic acid

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

Question 13

Predict the product for the following reaction.

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

Question 14

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 15

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 16

What is the IUPAC name for the following compound?

Question 17

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 18

What is the IUPAC name for the following compound?

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

Which one of the following compound is the strongest acid?

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

Question 21

Provide the structure for N-methylcyclohexanecarboxamide

Question 22

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 23

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

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

Question 24

Predict the product for the following reaction.

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

Question 25

Provide the structure for 3-ethylbenzonitrile.

Question 26

Provide the structure for benzyl propionate.

Question 27

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 28

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 29

Provide the structure for 4-ethylbenzoyl chloride

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

Question 30

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 31

Provide the structure for cyclopentanecarbonyl chloride

Question 32

What is the IUPAC name for the following compound?

Question 33

What is the IUPAC name for the following compound?

Question 34

What is the IUPAC name for the following compound?

Question 35

Provide the structure for benzoic ethanoic anhydride

Question 36

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 37

Provide the structure for acetic formic anhydride.

Question 38

Predict the product for the following reaction.

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

Question 39

What is the IUPAC name for the following compound?

Question 40

What is the common name for the following compound?

Question 41

Propose a stepwise synthesis for N-propylbutaneamide,using 1-proanol and/or carbon dioxide as your only source of carbon and using any other reagents necessary.

Question 42

Predict the product for the following reaction.

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

Question 43

Propose a stepwise synthesis for 2-phenylethanoyl chloride,using toluene and/or carbon dioxide as your only source of carbon and using any other reagents necessary.

Question 44

A compound with molecular formula C₈H₁₄O₃ exhibits a triplet at $\delta$ 1.0 (I=6),a sextet at $\delta$ 1.6 (I=4)and a triplet at $\delta$ 2.2 (I=4)in its ¹HNMR spectrum.Its IR spectrum shows two strong absorption bands near 1850 & 1750 cm^-1.What is the structure for this compound?

Question 45

Using ethyl-3-methylybutanoate as your only source of carbon and using any other reagents necessary,propose a stepwise synthesis for the following conversion.

Question 46

Using ethyl-3-methylybutanoate as your only source of carbon and using any other reagents necessary,propose a stepwise synthesis for the following conversion.

Question 47

Propose a stepwise synthesis for the following conversion.

Question 48

Predict the product for the following reaction.

Question 49

A compound with molecular formula C₈H₁₄O₄ exhibits a triplet at $\delta$ 1.3 (I=6),a singlet at $\delta$ 2.6 (I=4)and a quartet at $\delta$ 4.2 (I=4)in its ¹HNMR spectrum.Its IR spectrum shows a strong absorption band near 1740 cm^-1.What is the structure for this compound?

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

Question 50

A compound with molecular formula C₉H₁₀O₂ exhibits a triplet at $\delta$ 1.2 (I=3),a quartet at $\delta$ 2.6 (I=2),a doublet at $\delta$ 7.3 (I=2),a doublet at $\delta$ 8.0 (I=2)and a singlet at $\delta$ 11 (I=1)in its ¹HNMR spectrum.What is the structure for this compound?

Question 51

Predict the product for the following reaction.

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

Question 52

Predict the product for the following reaction.

Question 53

Predict the product for the following reaction.

Question 54

Predict the product for the following reaction and provide a stepwise curved arrow mechanism for the formation of product.

Question 55

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

A)
B)
C)
D)
E)A & C

Question 56

A compound with molecular formula C₆H₁₂O₂ exhibits two singlet in its ¹HNMR spectrum,at $\delta$ 1.4 (I=9)and $\delta$ 2.0 (I=3).Its IR spectrum shows a strong absorption band near 1740 cm^-1.What is the structure for this compound?

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

Question 57

Predict the product for the following reaction.

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

Question 58

Predict the product for the following reaction.