Question 1

How could you perform the following transformation?

Accepted Answer

1) NaCN
2)

Question 2

What compound results when benzoic acid reacts with methylamine, and what compound ultimately results when the initially formed compound is heated at

Accepted Answer

The answer of What compound results when benzoic acid reacts...

Question 3

Propose a synthesis of methyl thioacetate from one carbon compounds and any other necessary inorganic reagents.

Accepted Answer

Beginning with CO₂, 1

Question 4

Using ethanol as your only source of carbon compounds and using any other necessary inorganic reagents, propose a synthesis of acetonitrile.

Accepted Answer

Beginning with ethan

Question 5

What compound results when ethyl benzoate is stirred in methanol containing a trace of HCl and by what name is this process known?

Accepted Answer

methyl ben

Question 6

Provide the major organic product of the following reaction.

Accepted Answer

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

Question 7

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 
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 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

Why would you use acetic anhydride to do the following reaction as opposed to acetyl chloride?

Accepted Answer

Acetic anhydride is inexpensiv

Question 10

Lithium aluminum hydride reduces carboxylic acids, acid chlorides, and esters to ________.

Accepted Answer

A)  aldehydes 
B)  primary alcohols 
C)  secondary alcohols 
D)  tertiary alcohols 
E)  ketones 
A)  aldehydes 
B)  primary alcohols 
C)  secondary alcohols 
D)  tertiary alcohols 
E)  ketones

Question 11

Which of the following reactions is favorable, in the direction indicated, under fairly "normal" laboratory conditions?

Accepted Answer

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

Question 12

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 13

Provide the structure of propanoic anhydride.

Accepted Answer

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

Question 14

Arrange the following three amides in order of increasing boiling point: propanamide, N-methylacetamide, and N,N-dimethylformamide.

Accepted Answer

N,N-dimethylformamid

Question 15

Provide the structure of cyclohexyl formate.

Accepted Answer

The answer of Provide the structure of cyclohexyl formate....

Question 16

List the following four carboxylic acid derivatives, ester, anhydride, amide, and acid halide, in order of increasing reactivity in nucleophilic acyl substitution reactions. Start with the least reactive derivative.

Accepted Answer

amide < es

Question 17

Which of the following compound(s), 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 18

Using ethanol as your only source of carbon compounds and using any other necessary inorganic reagents, propose a synthesis of ethyl acetate.

Accepted Answer

Beginning with ethan

Question 19

Carbonated beverages typically have pHs below 7.0. What acid is present which lowers the pH? Show the reaction by which it is formed.

Accepted Answer

carbonic a

Question 20

Which of the following are strongly hydrogen bonded in the liquid phase?

Accepted Answer

A)  nitriles 
B)  esters 
C)  secondary amides 
D)  tertiary amides 
E)  acid chlorides 
A)  nitriles 
B)  esters 
C)  secondary amides 
D)  tertiary amides 
E)  acid chlorides

Exam 21: Carboxylic Acid Derivatives

How could you perform the following transformation?

What compound results when benzoic acid reacts with methylamine, and what compound ultimately results when the initially formed compound is heated at

Propose a synthesis of methyl thioacetate from one carbon compounds and any other necessary inorganic reagents.

Using ethanol as your only source of carbon compounds and using any other necessary inorganic reagents, propose a synthesis of acetonitrile.

What compound results when ethyl benzoate is stirred in methanol containing a trace of HCl and by what name is this process known?

Provide the major organic product of the following reaction.

In nucleophilic acyl substitution ________.

Provide the major organic product in the reaction shown below.

Why would you use acetic anhydride to do the following reaction as opposed to acetyl chloride?

Lithium aluminum hydride reduces carboxylic acids, acid chlorides, and esters to ________.

Which of the following reactions is favorable, in the direction indicated, under fairly "normal" laboratory conditions?

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

Provide the structure of propanoic anhydride.

Arrange the following three amides in order of increasing boiling point: propanamide, N-methylacetamide, and N,N-dimethylformamide.

Provide the structure of cyclohexyl formate.

List the following four carboxylic acid derivatives, ester, anhydride, amide, and acid halide, in order of increasing reactivity in nucleophilic acyl substitution reactions. Start with the least reactive derivative.

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

Using ethanol as your only source of carbon compounds and using any other necessary inorganic reagents, propose a synthesis of ethyl acetate.

Carbonated beverages typically have pHs below 7.0. What acid is present which lowers the pH? Show the reaction by which it is formed.

Which of the following are strongly hydrogen bonded in the liquid phase?

Structure and Bonding

Acids and Bases; Functional Groups

Structure and Stereochemistry of Alkanes

The Study of Chemical Reactions

Stereochemistry

Alkyl Halides; Nucleophilic Substitution

Structure and Synthesis of Alkenes; Elimination

Reactions of Alkenes

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

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