Question 1

Using potential energy diagrams, explain why alkoxides act as leaving groups in nucleophilic acyl substitutions but not in SN2 reactions.

Accepted Answer

See Figure 21-10, p.963 in the textbook.

Question 2

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 3

A correct order of reactivity of acid derivatives towards nucleophilic attack is:

Accepted Answer

A)  esters > acid anhydrides > amides. 
B)  anhydrides > amides > esters. 
C)  carboxylates > esters > amides. 
D)  anhydrides > acids > acid chlorides. 
E)  anhydrides > amides > carboxylates. 
A)  esters > acid anhydrides > amides. 
B)  anhydrides > amides > esters. 
C)  carboxylates > esters > amides. 
D)  anhydrides > acids > acid chlorides. 
E)  anhydrides > amides > carboxylates.

Question 4

Cyclic esters are called:

Accepted Answer

A)  lactones. 
B)  lactams. 
C)  lacrimals. 
D)  imides. 
E)  enamines. 
A)  lactones. 
B)  lactams. 
C)  lacrimals. 
D)  imides. 
E)  enamines.

Question 5

Arrange the carboxylic acid derivatives below in order of increasing reactivity towards nucleophilic acyl substitution.

Accepted Answer

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

Question 6

Provide the major organic product in the reaction shown below.

Accepted Answer

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

Question 7

Ethylene glycol will react with phosgene to produce what organic compound?

Accepted Answer

The answer of Ethylene glycol will react with phosgene to...

Question 8

Predict the major product of the following reaction.

Accepted Answer

The answer of Predict the major product of the following...

Question 9

Provide the major organic product in the reaction shown below.

Accepted Answer

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

Question 10

Predict the major product of the following reaction.

Accepted Answer

The answer of Predict the major product of the following...

Question 11

Provide the structure of N,N-diethylbutanamide.

Accepted Answer

The answer of Provide the structure of N,N-diethylbutanamide....

Question 12

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 13

Draw the product resulting from the following reaction. Indicate any relevant stereochemistry.

Accepted Answer

The answer of Draw the product resulting from the following...

Question 14

Provide the proper IUPAC name for the compound below.

Accepted Answer

3,3-dimeth

Question 15

The hydrolysis of esters in base is called:

Accepted Answer

A)  the Fischer esterification. 
B)  the Hunsdiecker reaction. 
C)  the Dieckmann condensation. 
D)  transesterification. 
E)  saponification. 
A)  the Fischer esterification. 
B)  the Hunsdiecker reaction. 
C)  the Dieckmann condensation. 
D)  transesterification. 
E)  saponification.

Question 16

Predict the major product of the following reaction.

Accepted Answer

The answer of Predict the major product of the following...

Question 17

Two equivalents of methyl magnesium bromide will add to:

Accepted Answer

A)  lactones. 
B)  aldehydes. 
C)  ketones. 
D)  imines. 
E)  secondary amines. 
A)  lactones. 
B)  aldehydes. 
C)  ketones. 
D)  imines. 
E)  secondary amines.

Question 18

What type of compound results from the reaction of ethyl formate with cyclohexylamine?

Accepted Answer

A)  amide 
B)  1° amine 
C)  acid anhydride 
D)  nitrile 
E)  carboxylate 
A)  amide 
B)  1° amine 
C)  acid anhydride 
D)  nitrile 
E)  carboxylate

Question 19

Provide the name of CH3O2CH2CH2CH2CH3.

Accepted Answer

Question 20

Which of the following is the most reactive carboxylic acid derivative?

Accepted Answer

A)  ester 
B)  anhydride 
C)  nitrile 
D)  acid chloride 
E)  amide 
A)  ester 
B)  anhydride 
C)  nitrile 
D)  acid chloride 
E)  amide

Exam 21: Carboxylic Acid Derivatives

Using potential energy diagrams, explain why alkoxides act as leaving groups in nucleophilic acyl substitutions but not in SN2 reactions.

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

A correct order of reactivity of acid derivatives towards nucleophilic attack is:

Cyclic esters are called:

Arrange the carboxylic acid derivatives below in order of increasing reactivity towards nucleophilic acyl substitution.

Provide the major organic product in the reaction shown below.

Ethylene glycol will react with phosgene to produce what organic compound?

Predict the major product of the following reaction.

Provide the major organic product in the reaction shown below.

Predict the major product of the following reaction.

Provide the structure of N,N-diethylbutanamide.

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

Draw the product resulting from the following reaction. Indicate any relevant stereochemistry.

Provide the proper IUPAC name for the compound below.

The hydrolysis of esters in base is called:

Predict the major product of the following reaction.

Two equivalents of methyl magnesium bromide will add to:

What type of compound results from the reaction of ethyl formate with cyclohexylamine?

Provide the name of CH3O2CH2CH2CH2CH3.

Which of the following is the most reactive carboxylic acid derivative?

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

Using potential energy diagrams, explain why alkoxides act as leaving groups in nucleophilic acyl substitutions but not in S_N2 reactions.

_{Cyclic esters are called:}

Provide the name of CH₃O₂CH₂CH₂CH₂CH₃.