Question 1

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

Accepted Answer

acetic aci

Question 2

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. 
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 3

Provide the name of the compound shown below.

Accepted Answer

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

Question 4

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

Accepted Answer

Their enhanced react

Question 5

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 6

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

Question 7

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). 
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 8

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

Question 9

Provide the structure of trifluoroacetic anhydride.

Accepted Answer

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

Question 10

Propose a synthesis of PhNHCHO from benzene.

Accepted Answer

1. HNO₃, H₂S

Question 11

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. 
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 12

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 13

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

Accepted Answer

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

Question 14

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

Question 15

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

Question 16

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 17

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

Question 18

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 19

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

Question 20

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

Accepted Answer

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

Exam 21: Carboxylic Acid Derivatives

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

The correct priority of functional groups in IUPAC nomenclature is:

Provide the name of the compound shown below.

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

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.

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

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

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

Provide the structure of trifluoroacetic anhydride.

Propose a synthesis of PhNHCHO from benzene.

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

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

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

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

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

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

Which of the following structures are carboxylic acid derivatives?

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

Phthalic acid produces what acid derivative upon heating?

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

Introduction and Review

Structure and Properties of Organic Molecules

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides: Nucleophilic Substitution and Elimination

Structure and Synthesis of Alkenes

Reactions of Alkenes

Alkynes

Structure and Synthesis of Alcohols

Reactions of Alcohols

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Ethers, Epoxides, and Thioethers

Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy

Aromatic Compounds

Reactions of Aromatic Compounds

Ketones and Aldehydes

Amines

Carboxylic Acids

Condensations and Alpha Substitutions of Carboxyl Compounds

Carbohydrates and Nucleic Acids

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

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

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

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