Question 1

The most characteristic IR stretch of butanenitrile occurs at approximately what wavenumber?

Accepted Answer

A)   3500 cm-1
B)   3100 cm-1
C)   2600 cm-1
D)   2200 cm-1
E)   1750 cm-1

Question 2

Identify the correct IUPAC systematic name for the structure below.

Accepted Answer

A)   N-methyl-2-ethyl-5-methyloctanamide
B)   6,N-dimethylnonane-3-carboxamide
C)   5,N-dimethyl-2-ethyloctanamide
D)   2-ethyl-5,N-dimethyloctanamide

Question 3

What reagents are used to dehydrate amides to nitriles?

Accepted Answer

The answer of What reagents are used to dehydrate amides...

Question 4

Provide the name of the compound shown below.

Accepted Answer

N, N-dimet...

Question 5

Provide the major organic product in the reaction shown below.

Accepted Answer

The answer of Provide the major organic product in the...

Question 6

Give two different one-step methods to convert propanoic acid to methyl propanoate.

Accepted Answer

1. Fischer esterific...

Question 7

Provide a detailed, stepwise mechanism for the reaction of  with ammonia.

Accepted Answer

The answer of Provide a detailed, stepwise mechanism for the...

Question 8

Provide the major organic product in the reaction shown below.

Accepted Answer

The answer of Provide the major organic product in the...

Question 9

Provide the major organic product in the reaction of CH3CH2CONH2 with hot aqueous acid.

Accepted Answer

Question 10

Acids can be reduced to aldehydes by:

Accepted Answer

A)   treatment with LiAlH4.
B)   conversion to the acid chloride followed by treatment with LiAlH[OC(CH3) 3]3.
C)   conversion to the amide followed by treatment with NaBH4.
D)   conversion to the ester followed by treatment with LiAlH4.
E)   conversion to the anhydride followed by treatment with Mg and H3O+.

Question 11

N-Methylacetamide is an example of:

Accepted Answer

A)   a primary amide.
B)   a secondary amide.
C)   a tertiary amide.
D)   an N, N-disubstituted amide.
E)   an imine

Question 12

Which sequence correctly lists the following structures in order of increasing rate of hydrolysis to a carboxylic acid under basic conditions?

Accepted Answer

A)   1 
B)   2 
C)   3 
D)   3 
E)   2 < 1 < 3

Question 13

Which of the following reagents convert(s)  benzoyl chloride to phenyl propyl ketone?

Accepted Answer

A)   CH3CH2CH2MgBr
B)   CH3CH2CH2Li
C)   (CH3CH2CH2) 2CuLi
D)   both A and B
E)   both A and C

Question 14

In nucleophilic acyl substitution,

Accepted Answer

A)   protonation of the carbonyl is followed immediately by loss of the leaving group.
B)   loss of the leaving group is followed by rearrangement of the carbocation.
C)   addition to the carbonyl by a nucleophile is followed by loss of the leaving group.
D)   ester hydrolysis is followed by deprotonation.
E)   an SN2 reaction occurs.

Question 15

While the carbonyl stretching frequency for simple aldehydes, ketones, and carboxylic acids is about 1710 cm-1, the carbonyl stretching frequency for amides is about ________.

Accepted Answer

A)   1700 cm-1
B)   1735 cm-1
C)   1800 cm-1
D)   1660 cm-1
E)   2200 cm-1

Question 16

What is the predicted major product of the following reaction?

Accepted Answer

A)  
B)  
C)  
D)  
E)

Question 17

Propose a synthesis of benzonitrile from benzene and any other necessary reagents.

Accepted Answer

1. HNO₃, H₂S...

Question 18

Provide the IUPAC name for HCONHCH2CH2CH3.

Accepted Answer

Question 19

Provide the major organic product of the following reaction.

Accepted Answer

The answer of Provide the major organic product of the...

Question 20

Provide the major organic product of the following reaction.

Accepted Answer

The answer of Provide the major organic product of the...

Exam 21: Carboxylic Acid Derivatives

Identify the correct IUPAC systematic name for the structure below.

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The most characteristic IR stretch of butanenitrile occurs at approximately what wavenumber?

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Provide the major organic product in the reaction shown below.

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Provide the IUPAC name for HCONHCH2CH2CH3.

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Provide the major organic product of the following reaction.

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Provide the name of the compound shown below.

Correct AnswerverifiedN, N-dimet...View AnswerShow Answer

Which sequence correctly lists the following structures in order of increasing rate of hydrolysis to a carboxylic acid under basic conditions?

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Provide the major organic product of the following reaction.

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Which of the following reagents convert(s) benzoyl chloride to phenyl propyl ketone?

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N-Methylacetamide is an example of:

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Provide the major organic product in the reaction shown below.

Correct AnswerverifiedShow Answer

What is the predicted major product of the following reaction?

Correct AnswerverifiedShow Answer

In nucleophilic acyl substitution,

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Provide the major organic product in the reaction of CH3CH2CONH2 with hot aqueous acid.

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While the carbonyl stretching frequency for simple aldehydes, ketones, and carboxylic acids is about 1710 cm-1, the carbonyl stretching frequency for amides is about ________.

Correct AnswerverifiedShow Answer

Give two different one-step methods to convert propanoic acid to methyl propanoate.

Correct Answerverified1. Fischer esterific...View AnswerShow Answer

Provide a detailed, stepwise mechanism for the reaction of with ammonia.

Correct AnswerverifiedShow Answer

Acids can be reduced to aldehydes by:

Correct AnswerverifiedShow Answer

Propose a synthesis of benzonitrile from benzene and any other necessary reagents.

Correct Answerverified1. HNO3, H2S...View AnswerShow Answer

What reagents are used to dehydrate amides to nitriles?

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Provide the IUPAC name for HCONHCH₂CH₂CH₃.

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N, N-dimet...
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Provide the major organic product in the reaction of CH₃CH₂CONH₂ with hot aqueous acid.

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While the carbonyl stretching frequency for simple aldehydes, ketones, and carboxylic acids is about 1710 cm^-1, the carbonyl stretching frequency for amides is about ________.

Correct Answer
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1. Fischer esterific...
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1. HNO₃, H₂S...
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Correct Answer
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