Question 1

Which one of the following has two different enol forms?

Accepted Answer

A)  cyclohexanone 
B)  3,3-dimethylcyclohexanone 
C)  2,2-dimethylcyclohexanone 
D)  4,4-dimethylcyclohexanone 
A)  cyclohexanone 
B)  3,3-dimethylcyclohexanone 
C)  2,2-dimethylcyclohexanone 
D)  4,4-dimethylcyclohexanone B

Question 2

What would result from treating (-)-menthone with basic $\mathrm{D}_{2} \mathrm{O}$ ?

Accepted Answer

A)  
  
B)  
  
C)  
  
D)  more than one of these is formed 
A)  
  
B)  
  
C)  
  
D)  more than one of these is formed D

Question 3

Identify the starting reagent needed to make the following cyclic ketone by an intramolecular aldol condensation reaction.

Accepted Answer

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

Question 4

The Robinson annulation reaction is shown below. Identify the missing reagent in the first step.

Accepted Answer

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

Question 5

What is the product of the reaction below?

Accepted Answer

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

Question 6

Which one of the following optically active compounds racemizes in dilute $\mathrm{KOH} / \mathrm{CH}_{3} \mathrm{OH}$ solution?

Accepted Answer

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

Question 7

Identify the most acidic hydrogen in the following compound.

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
A)  1 
B)  2 
C)  3 
D)  4

Question 8

What is the aldol addition product of propanal?

Accepted Answer

A)  2-hydroxy-2-methylpentanal 
B)  3-hydroxy-2-methylpentanal 
C)  3-hydroxyhexanal 
D)  4-hydroxyhexanal 
A)  2-hydroxy-2-methylpentanal 
B)  3-hydroxy-2-methylpentanal 
C)  3-hydroxyhexanal 
D)  4-hydroxyhexanal

Question 9

Which of the following is the Michael addition product of the reaction below?

Accepted Answer

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

Question 10

Which of the following is the Claisen condensation product of ethyl propanoate, $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{Et}$ ?

Accepted Answer

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

Question 11

Identify the missing reagent in the reaction shown below.

Accepted Answer

A)  ethyl formate, $\mathrm{HCO}_{2} \mathrm{Et}$ 
B)  diethyl carbonate, $(\mathrm{EtO})_{2} \mathrm{C}=\mathrm{O}$ 
C)  diethyl oxalate, $\mathrm{EtO}_{2} \mathrm{CCO}_{2} \mathrm{Et}$ 
D)  ethyl acetate, $\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{Et}$ 
A)  ethyl formate, $\mathrm{HCO}_{2} \mathrm{Et}$ 
B)  diethyl carbonate, $(\mathrm{EtO})_{2} \mathrm{C}=\mathrm{O}$ 
C)  diethyl oxalate, $\mathrm{EtO}_{2} \mathrm{CCO}_{2} \mathrm{Et}$ 
D)  ethyl acetate, $\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{Et}$

Question 12

Which one of the following cannot form an enolate anion?

Accepted Answer

A)  2,2-dimethylbutanal 
B)  2,3-dimethylbutanal 
C)  2-ethylbutanal 
D)  3,3-dimethylbutanal 
A)  2,2-dimethylbutanal 
B)  2,3-dimethylbutanal 
C)  2-ethylbutanal 
D)  3,3-dimethylbutanal

Question 13

The compound shown below undergoes a retro (reverse) aldol reaction under these conditions. What product(s) result(s)?

Accepted Answer

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

Question 14

What is the missing reagent in the synthesis shown below?

Accepted Answer

A)  bromocyclopentane 
B)  1,4-dibromobutane 
C)  1,5-dibromopentane 
D)  1,1-dibromocyclopentane 
A)  bromocyclopentane 
B)  1,4-dibromobutane 
C)  1,5-dibromopentane 
D)  1,1-dibromocyclopentane

Which one of the following has two different enol forms?

What would result from treating (-)-menthone with basic $\mathrm{D}_{2} \mathrm{O}$ ? $What would result from treating (-)-menthone with basic \mathrm{D}_{2} \mathrm{O} ?$

Identify the starting reagent needed to make the following cyclic ketone by an intramolecular aldol condensation reaction.

The Robinson annulation reaction is shown below. Identify the missing reagent in the first step.

What is the product of the reaction below?

Which one of the following optically active compounds racemizes in dilute $\mathrm{KOH} / \mathrm{CH}_{3} \mathrm{OH}$ solution?

Identify the most acidic hydrogen in the following compound.

What is the aldol addition product of propanal?

Which of the following is the Michael addition product of the reaction below?

Which of the following is the Claisen condensation product of ethyl propanoate, $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{Et}$ ?

Identify the missing reagent in the reaction shown below.

Which one of the following cannot form an enolate anion?

The compound shown below undergoes a retro (reverse) aldol reaction under these conditions. What product(s) result(s)?

What is the missing reagent in the synthesis shown below?

Structure Determines Properties

Alkanes and Cycloakanes: Introduction to Hydrocarbons

Alkanes and Cycloalkanes: Introduction to Stereochemistry

Alcohols and Alkyl Halides: Introduction to Reaction Mechanisms

Structure and Preparation of Alkenes: Elimination Reactions

Addition Reactions of Alkenes

Chirality

Nucleophilic Substitution

Alkynes

Spectroscopy

Organometallic Compounds

Alcohols, Diols, and Thiols

Ethers, Epoxides, and Sulfides

Aldehydes and Ketones: Nucleophilic Addition to the Carbonyl Group

Carboxylic Acids

Acid Derivatives

Amines

Phenols

Carbohydrates

Lipids

Amino Acids, Peptides, and Proteins

Nucleosides, Nucleotides, and Nucleic Acids

Synthetic Polymers

Filters

Exam 20: Enols and Enolates

Which one of the following has two different enol forms?

What would result from treating (-)-menthone with basic D2O\mathrm{D}_{2} \mathrm{O}D2​O ?

Identify the starting reagent needed to make the following cyclic ketone by an intramolecular aldol condensation reaction.

The Robinson annulation reaction is shown below. Identify the missing reagent in the first step.

What is the product of the reaction below?

Which one of the following optically active compounds racemizes in dilute KOH/CH3OH\mathrm{KOH} / \mathrm{CH}_{3} \mathrm{OH}KOH/CH3​OH solution?

Identify the most acidic hydrogen in the following compound.

What is the aldol addition product of propanal?

Which of the following is the Michael addition product of the reaction below?

Which of the following is the Claisen condensation product of ethyl propanoate, CH3CH2CO2Et\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{Et}CH3​CH2​CO2​Et ?

Identify the missing reagent in the reaction shown below.

Which one of the following cannot form an enolate anion?

The compound shown below undergoes a retro (reverse) aldol reaction under these conditions. What product(s) result(s)?

What is the missing reagent in the synthesis shown below?

Structure Determines Properties

Alkanes and Cycloakanes: Introduction to Hydrocarbons

Alkanes and Cycloalkanes: Introduction to Stereochemistry

Alcohols and Alkyl Halides: Introduction to Reaction Mechanisms

Structure and Preparation of Alkenes: Elimination Reactions

Addition Reactions of Alkenes

Chirality

Nucleophilic Substitution

Alkynes

Spectroscopy

Organometallic Compounds

Alcohols, Diols, and Thiols

Ethers, Epoxides, and Sulfides

Aldehydes and Ketones: Nucleophilic Addition to the Carbonyl Group

Carboxylic Acids

Acid Derivatives

Amines

Phenols

Carbohydrates

Lipids

Amino Acids, Peptides, and Proteins

Nucleosides, Nucleotides, and Nucleic Acids

Synthetic Polymers

Filters

What would result from treating (-)-menthone with basic $\mathrm{D}_{2} \mathrm{O}$ ? $What would result from treating (-)-menthone with basic \mathrm{D}_{2} \mathrm{O} ?$

Which one of the following optically active compounds racemizes in dilute $\mathrm{KOH} / \mathrm{CH}_{3} \mathrm{OH}$ solution?

Which of the following is the Claisen condensation product of ethyl propanoate, $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{Et}$ ?