Question 1

What compound is produced when N,N-dimethylpropanamide is treated with LiAlH4?

Accepted Answer

A)   CH3CH2CONH2
B)   CH3CH2CH2NH2
C)   CH3CH2CH2OH
D)   CH3CH2CH2N(CH3) 2
E)   CH3CH2N(CH3) 2

Question 2

What are the major organic products when 1 equivalent of acetic formic anhydride reacts with 1 equivalent of methanol?

Accepted Answer

acetic aci...

Question 3

List the following five compounds, ethanamide, 1-propanol, methyl formate, acetic acid, and propanenitrile, in order of increasing boiling point. Start with the lowest boiling compound.

Accepted Answer

methyl formate < pro...

Question 4

Which compound has a carbonyl stretch in its IR spectrum at the lowest wavenumber?

Accepted Answer

A)   acetic anhydride
B)   formamide
C)   cyclohexanone
D)   propanoyl chloride
E)   ethyl acetate

Question 5

Provide the structure of 2-bromo-2-methylbutanoyl chloride.

Accepted Answer

The answer of Provide the structure of 2-bromo-2-methylbutanoyl chloride....

Question 6

In 1H NMR, the chemical shifts for protons α to a carbonyl group:

Accepted Answer

A)   are similar for all acid derivatives.
B)   are farthest downfield for carboxylic acids.
C)   are farther downfield than those α to a nitrile.
D)   fall between δ 3.1 and δ 4.2 (ppm) .
E)   fall between δ 1.3 and δ 1.8 (ppm) .

Question 7

Which of the following structures are carboxylic acid derivatives?

Accepted Answer

A)   3
B)   1 & 3
C)   1, 2, & 3
D)   4
E)   All are carboxylic acid derivatives.

Question 8

Using resonance structures and pictures of orbitals, explain why resonance stabilization of thioesters is less than that of esters.

Accepted Answer

See Figure 21-12 on p.989 in t...

Question 9

Predict the product that results from 2-methylamino-1-ethanol being treated with phosgene.

Accepted Answer

The answer of Predict the product that results from 2-methylamino-1-ethanol...

Question 10

Propose a synthesis of PhNHCHO from benzene.

Accepted Answer

1. HNO₃, H₂S...

Question 11

Which of the following compounds, when reacted with aniline, yield(s)  acetanilide?

Accepted Answer

A)   acetyl chloride
B)   acetic anhydride
C)   methyl butanoate
D)   both A and B
E)   both A and C

Question 12

Why are β-lactams, such as penicillins and cephalosporins, unusually reactive amides?

Accepted Answer

Their enhanced react...

Question 13

In the proton NMR spectrum of a secondary amide, the amide proton's signal is:

Accepted Answer

A)   sharp, around δ 5.0 (ppm) .
B)   sharp, around δ 10.0 (ppm) .
C)   broad, around δ 9.0 (ppm) .
D)   broad, around δ 7.0 (ppm) .
E)   usually not observed.

Question 14

Provide the name of the compound shown below.

Accepted Answer

The answer of Provide the name of the compound shown...

Question 15

The correct priority of functional groups in IUPAC nomenclature is:

Accepted Answer

A)   ester > amide > ketone > acid.
B)   ketone > acid > ester > amide.
C)   acid > ester > amide > ketone.
D)   amide > acid > ester > ketone.
E)   amide > ester > acid > ketone.

Question 16

Complete the following reaction by filling in the necessary starting material.

Accepted Answer

The answer of Complete the following reaction by filling in...

Question 17

Phthalic acid produces what acid derivative upon heating?

Accepted Answer

A)   an ester
B)   a carboxylate
C)   an acid chloride
D)   an anhydride
E)   an amide

Question 18

A nitrile can be made by dehydrating an amide. However, for this reaction to occur, the amide must be:

Accepted Answer

A)   primary.
B)   secondary.
C)   tertiary.
D)   N-methylated.
E)   part of a lactam.

Question 19

Provide a detailed, stepwise mechanism for the reaction of propanoic anhydride with phenol.

Accepted Answer

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

Question 20

Provide the structure of trifluoroacetic anhydride.

Accepted Answer

The answer of Provide the structure of trifluoroacetic anhydride....

Exam 21: Carboxylic Acid Derivatives

Phthalic acid produces what acid derivative upon heating?

Correct AnswerverifiedShow Answer

Provide the structure of trifluoroacetic anhydride.

Correct AnswerverifiedShow Answer

Provide a detailed, stepwise mechanism for the reaction of propanoic anhydride with phenol.

Correct AnswerverifiedShow Answer

List the following five compounds, ethanamide, 1-propanol, methyl formate, acetic acid, and propanenitrile, in order of increasing boiling point. Start with the lowest boiling compound.

Correct Answerverifiedmethyl formate < pro...View AnswerShow Answer

In 1H NMR, the chemical shifts for protons α to a carbonyl group:

Correct AnswerverifiedShow Answer

Which of the following compounds, when reacted with aniline, yield(s) acetanilide?

Correct AnswerverifiedShow Answer

A nitrile can be made by dehydrating an amide. However, for this reaction to occur, the amide must be:

Correct AnswerverifiedShow Answer

The correct priority of functional groups in IUPAC nomenclature is:

Correct AnswerverifiedShow Answer

Provide the structure of 2-bromo-2-methylbutanoyl chloride.

Correct AnswerverifiedShow Answer

Provide the name of the compound shown below.

Correct AnswerverifiedShow Answer

Which of the following structures are carboxylic acid derivatives?

Correct AnswerverifiedShow Answer

Why are β-lactams, such as penicillins and cephalosporins, unusually reactive amides?

Correct AnswerverifiedTheir enhanced react...View AnswerShow Answer

Complete the following reaction by filling in the necessary starting material.

Correct AnswerverifiedShow Answer

Predict the product that results from 2-methylamino-1-ethanol being treated with phosgene.

Correct AnswerverifiedShow Answer

Using resonance structures and pictures of orbitals, explain why resonance stabilization of thioesters is less than that of esters.

Correct AnswerverifiedSee Figure 21-12 on p.989 in t...View AnswerShow Answer

Which compound has a carbonyl stretch in its IR spectrum at the lowest wavenumber?

Correct AnswerverifiedShow Answer

In the proton NMR spectrum of a secondary amide, the amide proton's signal is:

Correct AnswerverifiedShow Answer

What compound is produced when N,N-dimethylpropanamide is treated with LiAlH4?

Correct AnswerverifiedShow Answer

What are the major organic products when 1 equivalent of acetic formic anhydride reacts with 1 equivalent of methanol?

Correct Answerverifiedacetic aci...View AnswerShow Answer

Propose a synthesis of PhNHCHO from benzene.

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

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified
methyl formate < pro...
View Answer

In ¹H NMR, the chemical shifts for protons α to a carbonyl group:

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified

_{The correct priority of functional groups in IUPAC nomenclature is:}

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified
Their enhanced react...
View Answer

Correct Answer
verified

Correct Answer
verified

Correct Answer
verified
See Figure 21-12 on p.989 in t...
View Answer

Correct Answer
verified

Correct Answer
verified

What compound is produced when N,N-dimethylpropanamide is treated with LiAlH₄?

Correct Answer
verified

Correct Answer
verified
acetic aci...
View Answer

Correct Answer
verified
1. HNO₃, H₂S...
View Answer