Question 1

Which of the following is the best Michael acceptor?

Accepted Answer

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

Question 2

Complete the following synthesis by filling in the missing reagents.

Accepted Answer

1) NaOMe 2) benzyl bromide 3) H₃O⁺, heat

Question 3

Disregarding stereoisomers, how many different enols can the β-diketone CH3COCH2COCH2CH3 form?

Accepted Answer

A)  0 
B)  1 
C)  2 
D)  3 
E)  4 
A)  0 
B)  1 
C)  2 
D)  3 
E)  4 E

Question 4

When 2-methylcyclohexanone is treated with catalytic base in excess D2O, how many deuterium atoms become incorporated in the organic compound?

Accepted Answer

A)  0 
B)  1 
C)  2 
D)  3 
E)  5 
A)  0 
B)  1 
C)  2 
D)  3 
E)  5

Question 5

Arrange the following compounds in order of increasing acidity:
acetone, ethyl acetoacetate, ethyl acetate, and ethanol.

Accepted Answer

ethyl acetate < acet

Question 6

Provide the structure of the product that results when diethyl malonate is subjected to the following sequence: 1. NaOCH2CH3  2. CH3CH2CH2CH2I 3. H3O+, heat.

Accepted Answer

Question 7

What crossed-aldol product results when butanal is heated in the presence of excess benzaldehyde and sodium hydroxide?

Accepted Answer

The answer of What crossed-aldol product results when butanal is...

Question 8

Which of the following is another name for the product of an aldol condensation?

Accepted Answer

A)  β-hydroxyaldehyde 
B)  α-hydroxyaldehyde 
C)  acetal 
D)  β-ketoester 
E)  1,3-dialdehyde 
A)  β-hydroxyaldehyde 
B)  α-hydroxyaldehyde 
C)  acetal 
D)  β-ketoester 
E)  1,3-dialdehyde

Question 9

Provide the structure of the major organic product which results when PhCO2CH2CH3 and CH3CH2CO2CH2CH3 are heated in the presence of sodium ethoxide and the compound generated is subsequently treated with cold, dilute acid.

Accepted Answer

Question 10

Provide the structure of the major organic product which results when PhCH2CHO is treated with NaOH.

Accepted Answer

Question 11

Provide the structure of the product that results when ethyl acetoacetate is subjected to the following sequence: 1. NaOCH2CH3 2. CH3CH2CH2CH2I 3. H3O+, heat.

Accepted Answer

Question 12

When compound X is heated, PhCOCH(CH3)2 and CO2 are produced. Offer a structure for compound X.

Accepted Answer

Question 13

Which of the following compounds will not undergo reaction with an enolate?

Accepted Answer

A)  1-pentene 
B)  bromine 
C)  propanal 
D)  1-bromobutane 
E)  benzoyl chloride 
A)  1-pentene 
B)  bromine 
C)  propanal 
D)  1-bromobutane 
E)  benzoyl chloride

Question 14

In the Michael reaction, addition to the α,β-unsaturated carbonyl occurs in a ________.

Accepted Answer

A)  1,2-fashion 
B)  1,3-fashion 
C)  1,4-fashion 
D)  1,5-fashion 
E)  Diels-Alder reaction 
A)  1,2-fashion 
B)  1,3-fashion 
C)  1,4-fashion 
D)  1,5-fashion 
E)  Diels-Alder reaction

Question 15

Provide a synthesis of the compound shown below from cyclopent-2-en-1-one and acetoacetic ester.

Accepted Answer

From acetoacetic est

Question 16

What type of reaction is shown below?

Accepted Answer

A)  Aldol condensation 
B)  Claisen Condensation 
C)  Michael Addition 
D)  Alkylation 
A)  Aldol condensation 
B)  Claisen Condensation 
C)  Michael Addition 
D)  Alkylation

Question 17

Provide the major organic product of the reaction shown below.

Accepted Answer

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

Question 18

Draw a mechanism and provide the structure of the aldol product that results when 4-methylpentanal is heated with sodium hydroxide.

Accepted Answer

The answer of Draw a mechanism and provide the structure...

Question 19

What product results when pentanal is heated with sodium hydroxide?

Accepted Answer

The answer of What product results when pentanal is heated...

Question 20

Show how the following compound can be synthesized using an Aldol Condensation reaction.

Accepted Answer

The answer of Show how the following compound can be...

Exam 22: Condensations and Alpha Substitutions of Carboxyl Compounds

Which of the following is the best Michael acceptor?

Complete the following synthesis by filling in the missing reagents.

Disregarding stereoisomers, how many different enols can the β-diketone CH3COCH2COCH2CH3 form?

When 2-methylcyclohexanone is treated with catalytic base in excess D2O, how many deuterium atoms become incorporated in the organic compound?

Arrange the following compounds in order of increasing acidity: acetone, ethyl acetoacetate, ethyl acetate, and ethanol.

Provide the structure of the product that results when diethyl malonate is subjected to the following sequence: 1. NaOCH2CH3 2. CH3CH2CH2CH2I 3. H3O+, heat.

What crossed-aldol product results when butanal is heated in the presence of excess benzaldehyde and sodium hydroxide?

Which of the following is another name for the product of an aldol condensation?

Provide the structure of the major organic product which results when PhCO2CH2CH3 and CH3CH2CO2CH2CH3 are heated in the presence of sodium ethoxide and the compound generated is subsequently treated with cold, dilute acid.

Provide the structure of the major organic product which results when PhCH2CHO is treated with NaOH.

Provide the structure of the product that results when ethyl acetoacetate is subjected to the following sequence: 1. NaOCH2CH3 2. CH3CH2CH2CH2I 3. H3O+, heat.

When compound X is heated, PhCOCH(CH3)2 and CO2 are produced. Offer a structure for compound X.

Which of the following compounds will not undergo reaction with an enolate?

In the Michael reaction, addition to the α,β-unsaturated carbonyl occurs in a ________.

Provide a synthesis of the compound shown below from cyclopent-2-en-1-one and acetoacetic ester.

What type of reaction is shown below?

Provide the major organic product of the reaction shown below.

Draw a mechanism and provide the structure of the aldol product that results when 4-methylpentanal is heated with sodium hydroxide.

What product results when pentanal is heated with sodium hydroxide?

Show how the following compound can be synthesized using an Aldol Condensation reaction.

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

Carboxylic Acid Derivatives

Carbohydrates and Nucleic Acids

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

Filters

Disregarding stereoisomers, how many different enols can the β-diketone CH₃COCH₂COCH₂CH₃ form?

When 2-methylcyclohexanone is treated with catalytic base in excess D₂O, how many deuterium atoms become incorporated in the organic compound?

Provide the structure of the product that results when diethyl malonate is subjected to the following sequence: 1. NaOCH₂CH₃ 2. CH₃CH₂CH₂CH₂I 3. H₃O⁺, heat.

Provide the structure of the major organic product which results when PhCO₂CH₂CH₃ and CH₃CH₂CO₂CH₂CH₃ are heated in the presence of sodium ethoxide and the compound generated is subsequently treated with cold, dilute acid.

Provide the structure of the major organic product which results when PhCH₂CHO is treated with NaOH.

Provide the structure of the product that results when ethyl acetoacetate is subjected to the following sequence: 1. NaOCH₂CH₃ 2. CH₃CH₂CH₂CH₂I 3. H₃O⁺, heat.

When compound X is heated, PhCOCH(CH₃)₂ and CO₂ are produced. Offer a structure for compound X.

In the Michael reaction, addition to theα,β-unsaturated carbonyl occurs in a ________.