Question 1

What reaction type is an Aldol reaction?

Accepted Answer

A)  nucleophilic substitution 
B)  electrophilic substitution 
C)  electrophilic addition 
D)  nucleophilic addition 
A)  nucleophilic substitution 
B)  electrophilic substitution 
C)  electrophilic addition 
D)  nucleophilic addition D

Question 2

Complete this statement: A major difference between the Aldol condensation and the Claisen condensation reactions is that

Accepted Answer

A)  the Aldol reaction involves substitution while the Claisen reaction involves addition. 
B)  the Aldol reaction is acid catalyzed while the Claisen reaction is base-catalyzed. 
C)  the Aldol reaction is base catalyzed while the Claisen reaction requires a full equivalent of base. 
D)  the Aldol reaction is base catalyzed while the Claisen reaction is acid-catalyzed. 
A)  the Aldol reaction involves substitution while the Claisen reaction involves addition. 
B)  the Aldol reaction is acid catalyzed while the Claisen reaction is base-catalyzed. 
C)  the Aldol reaction is base catalyzed while the Claisen reaction requires a full equivalent of base. 
D)  the Aldol reaction is base catalyzed while the Claisen reaction is acid-catalyzed. C

Question 3

What is the Aldol addition product formed from the reaction of (CH3)2CHCH2CHO with itself?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
A)  I 
B)  II 
C)  III 
D)  IV D

Question 4

What are the two starting materials for a Robinson annulation?

Accepted Answer

A)  an F1F1F1S1F1F1F10,F1F1F1S1F1F1F10-unsaturated carbonyl compound and an enolate 
B)  a F1F1F1S1F1F1F10-ketoester and an enolate 
C)  a 1,5-dicarbonyl compound and an enolate 
D)  a 1,3-dicarbonyl compound and an enolate 
A)  an F1F1F1S1F1F1F10,F1F1F1S1F1F1F10-unsaturated carbonyl compound and an enolate 
B)  a F1F1F1S1F1F1F10-ketoester and an enolate 
C)  a 1,5-dicarbonyl compound and an enolate 
D)  a 1,3-dicarbonyl compound and an enolate

Question 5

Would this crossed Aldol reaction work well? Why or why not?

Accepted Answer

A)  Yes, the diketone is significantly more acidic, so this enolate can be formed selectively. 
B)  Yes, the aldehyde is significantly more acidic, so this enolate can be formed selectively. 
C)  No, the aldehyde is significantly more acidic, so this enolate cannot be formed selectively. 
D)  No, the diketone is significantly more acidic, so this enolate cannot be formed selectively. 
A)  Yes, the diketone is significantly more acidic, so this enolate can be formed selectively. 
B)  Yes, the aldehyde is significantly more acidic, so this enolate can be formed selectively. 
C)  No, the aldehyde is significantly more acidic, so this enolate cannot be formed selectively. 
D)  No, the diketone is significantly more acidic, so this enolate cannot be formed selectively.

Question 6

Which is the unsaturated carbonyl compound is formed by the dehydration of the following F1F1F1S1F1F1F10-hydroxy carbonyl compound?

Accepted Answer

A)  I 
B)  II 
C)  I and II 
D)  None of the choices 
A)  I 
B)  II 
C)  I and II 
D)  None of the choices

Question 7

What is the Aldol addition product formed from reaction of the following compound with itself?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
A)  I 
B)  II 
C)  III 
D)  IV

Question 8

Under basic conditions, the Aldol reaction is reversible, but dehydration is not. What is the reason for this difference in reactivity?

Accepted Answer

A)  The initial Aldol product is an alkoxide, so the reaction is not energetically downhill in either direction. 
B)  The initial Aldol product is an alkoxide, so the reaction is energetically downhill going toward the product. 
C)  The initial Aldol product is an alkoxide, so the reaction is energetically downhill going toward the starting materials. 
D)  Water is a stable molecule. 
A)  The initial Aldol product is an alkoxide, so the reaction is not energetically downhill in either direction. 
B)  The initial Aldol product is an alkoxide, so the reaction is energetically downhill going toward the product. 
C)  The initial Aldol product is an alkoxide, so the reaction is energetically downhill going toward the starting materials. 
D)  Water is a stable molecule.

Question 9

Which of the following compounds cannot serve as a Michael acceptor?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
A)  I 
B)  II 
C)  III 
D)  IV

Question 10

Which of the following carbonyl compounds will undergo Aldol addition reactions when treated with aqueous sodium hydroxide?

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  None of the choices 
A)  I 
B)  II 
C)  III 
D)  None of the choices

Question 11

When is a crossed Aldol reaction said to be synthetically useful?

Accepted Answer

A)  When both carbonyl compounds have F1F1F1S1F1F1F10 hydrogens. 
B)  When both carbonyl compounds have no F1F1F1S1F1F1F10 hydrogens. 
C)  When one carbonyl compound has no F1F1F1S1F1F1F10 hydrogens. 
D)  When one carbonyl compound has no F1F1F1S1F1F1F10 hydrogens. 
A)  When both carbonyl compounds have F1F1F1S1F1F1F10 hydrogens. 
B)  When both carbonyl compounds have no F1F1F1S1F1F1F10 hydrogens. 
C)  When one carbonyl compound has no F1F1F1S1F1F1F10 hydrogens. 
D)  When one carbonyl compound has no F1F1F1S1F1F1F10 hydrogens.

Question 12

If a Claisen condensation reaction is run using methyl propanoate as the reactant, NaOCH3 is the ideal base. Why is it important to use NaOCH3 and not NaOCH2CH3?

Accepted Answer

A)  NaOCH3 is a stronger base than NaOCH2CH3, and this reaction requires a stronger base. 
B)  NaOCH3 is a weaker base than NaOCH2CH3, and this reaction requires a weaker base. 
C)  Transesterfication can occur when esters react, and this transesterfication would result in a mixture of products. 
D)  NaOCH3 is more soluble than NaOCH2CH3 in organic solvents, and this reaction requires a full equivalent of base to proceed. A full equivalent of NaOCH2CH3 would not dissolve, so the reaction would not proceed. 
A)  NaOCH3 is a stronger base than NaOCH2CH3, and this reaction requires a stronger base. 
B)  NaOCH3 is a weaker base than NaOCH2CH3, and this reaction requires a weaker base. 
C)  Transesterfication can occur when esters react, and this transesterfication would result in a mixture of products. 
D)  NaOCH3 is more soluble than NaOCH2CH3 in organic solvents, and this reaction requires a full equivalent of base to proceed. A full equivalent of NaOCH2CH3 would not dissolve, so the reaction would not proceed.

Question 13

The following reaction is an example of what type of reaction?

Accepted Answer

A)  Michael reaction 
B)  Aldol self-condensation 
C)  Dieckmann condensation 
D)  Robinson annulation 
A)  Michael reaction 
B)  Aldol self-condensation 
C)  Dieckmann condensation 
D)  Robinson annulation

Question 14

In a Michael reaction, where does the nucleophile attack the F1F1F1S1F1F1F10,F1F1F1S1F1F1F10-unsaturated carbonyl component?

Accepted Answer

A)  "F1F1F1S1F1F1F10-Carbon" 
B)  "F1F1F1S1F1F1F10-Carbon" 
C)  "Carbonyl carbon" 
D)  "Carbonyl carbon and F1F1F1S1F1F1F10-carbon" 
A)  "F1F1F1S1F1F1F10-Carbon" 
B)  "F1F1F1S1F1F1F10-Carbon" 
C)  "Carbonyl carbon" 
D)  "Carbonyl carbon and F1F1F1S1F1F1F10-carbon"

Question 15

What is the general name for the reaction product formed in an aldol addition reaction?

Accepted Answer

A)  "F1F1F1S1F1F1F10-hydroxy carbonyl compound." 
B)  "F1F1F1S1F1F1F10-hydroxy carbonyl compound." 
C)  "F1F1F1S1F1F1F10-hydroxy carbonyl compound." 
D)  "F1F1F1S1F1F1F10,F1F1F1S1F1F1F10-hydroxy carbonyl compound." 
A)  "F1F1F1S1F1F1F10-hydroxy carbonyl compound." 
B)  "F1F1F1S1F1F1F10-hydroxy carbonyl compound." 
C)  "F1F1F1S1F1F1F10-hydroxy carbonyl compound." 
D)  "F1F1F1S1F1F1F10,F1F1F1S1F1F1F10-hydroxy carbonyl compound."

Question 16

In the correct order, what are the three general steps in the mechanism of a Claisen reaction?

Accepted Answer

A)  Enolate formation, elimination, nucleophilic addition. 
B)  Enolate formation, nucleophilic addition, elimination. 
C)  Elimination, enolate formation, nucleophilic addition. 
D)  Nucleophilic addition, enolate formation, elimination. 
A)  Enolate formation, elimination, nucleophilic addition. 
B)  Enolate formation, nucleophilic addition, elimination. 
C)  Elimination, enolate formation, nucleophilic addition. 
D)  Nucleophilic addition, enolate formation, elimination.

Question 17

In what situation can the yield of a single crossed Aldol product be increased?

Accepted Answer

A)  The electrophilic carbonyl component is relatively unhindered and is used in excess. 
B)  The electrophilic carbonyl carbon component is relatively hindered and is used in limited amount. 
C)  The nucleophilic carbonyl component is relatively unhindered and is used in excess. 
D)  The nucleophilic carbonyl component is relatively hindered and is used in limited amount. 
A)  The electrophilic carbonyl component is relatively unhindered and is used in excess. 
B)  The electrophilic carbonyl carbon component is relatively hindered and is used in limited amount. 
C)  The nucleophilic carbonyl component is relatively unhindered and is used in excess. 
D)  The nucleophilic carbonyl component is relatively hindered and is used in limited amount.

Question 18

The following reaction is an example of what type of reaction?

Accepted Answer

A)  Claisen condensation 
B)  mixed Aldol reaction 
C)  Robinson annulation 
D)  Dieckmann condensation 
A)  Claisen condensation 
B)  mixed Aldol reaction 
C)  Robinson annulation 
D)  Dieckmann condensation

Question 19

Why is the Aldol reaction often called an Aldol condensation?

Accepted Answer

A)  The initially formed F1F1F1S1F1F1F10-hydroxy carbonyl compound loses a hydroxyl group. 
B)  The initially formed F1F1F1S1F1F1F10-hydroxy carbonyl compound loses an oxygen atom. 
C)  The initially formed F1F1F1S1F1F1F10-hydroxy carbonyl compound loses a hydrogen atom. 
D)  The initially formed F1F1F1S1F1F1F10-hydroxy carbonyl compound loses water. 
A)  The initially formed F1F1F1S1F1F1F10-hydroxy carbonyl compound loses a hydroxyl group. 
B)  The initially formed F1F1F1S1F1F1F10-hydroxy carbonyl compound loses an oxygen atom. 
C)  The initially formed F1F1F1S1F1F1F10-hydroxy carbonyl compound loses a hydrogen atom. 
D)  The initially formed F1F1F1S1F1F1F10-hydroxy carbonyl compound loses water.

Question 20

What is the general name of the product of a crossed Claisen reaction between a ketone and an ester?

Accepted Answer

A)  "F1F1F1S1F1F1F10-keto ester" 
B)  "F1F1F1S1F1F1F10,F1F1F1S1F1F1F10-dicarbonyl compound" 
C)  "F1F1F1S1F1F1F10-dicarbonyl compound" 
D)  "F1F1F1S1F1F1F10-dicarbonyl compound" 
A)  "F1F1F1S1F1F1F10-keto ester" 
B)  "F1F1F1S1F1F1F10,F1F1F1S1F1F1F10-dicarbonyl compound" 
C)  "F1F1F1S1F1F1F10-dicarbonyl compound" 
D)  "F1F1F1S1F1F1F10-dicarbonyl compound"

Exam 24: Carbonyl Condensation Reactions

What reaction type is an Aldol reaction?

Complete this statement: A major difference between the Aldol condensation and the Claisen condensation reactions is that

What is the Aldol addition product formed from the reaction of (CH3)2CHCH2CHO with itself?

What are the two starting materials for a Robinson annulation?

Would this crossed Aldol reaction work well? Why or why not?

Which is the unsaturated carbonyl compound is formed by the dehydration of the following -hydroxy carbonyl compound?

What is the Aldol addition product formed from reaction of the following compound with itself?

Under basic conditions, the Aldol reaction is reversible, but dehydration is not. What is the reason for this difference in reactivity?

Which of the following compounds cannot serve as a Michael acceptor?

Which of the following carbonyl compounds will undergo Aldol addition reactions when treated with aqueous sodium hydroxide?

When is a crossed Aldol reaction said to be synthetically useful?

If a Claisen condensation reaction is run using methyl propanoate as the reactant, NaOCH3 is the ideal base. Why is it important to use NaOCH3 and not NaOCH2CH3?

The following reaction is an example of what type of reaction?

In a Michael reaction, where does the nucleophile attack the ,-unsaturated carbonyl component?

What is the general name for the reaction product formed in an aldol addition reaction?

In the correct order, what are the three general steps in the mechanism of a Claisen reaction?

In what situation can the yield of a single crossed Aldol product be increased?

The following reaction is an example of what type of reaction?

Why is the Aldol reaction often called an Aldol condensation?

What is the general name of the product of a crossed Claisen reaction between a ketone and an ester?

Structure and Bonding

Acids and Bases

Introduction to Organic Molecules and Functional Groups

Alkanes

Stereochemistry

Understanding Organic Reactions

Alkyl Halides and Nucleophilic Substitution

Alkyl Halides and Elimination Reactions

Alcohols, Ethers and Epoxides

Alkenes

Alkynes

Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Radical Reactions

Conjugation, Resonance, and Dienes

Benzene and Aromatic Compounds

Electrophilic Aromatic Substitution

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones Nucleophilic Addition

Carboxylic Acids and Derivatives

Substitution Reactions of Carbonyl Compounds at the Alpha-Carbon

Amines

Carbon-Carbon Bond Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Lipids

Synthetic Polymers

Filters

What is the Aldol addition product formed from the reaction of (CH₃)₂CHCH₂CHO with itself?

If a Claisen condensation reaction is run using methyl propanoate as the reactant, NaOCH₃ is the ideal base. Why is it important to use NaOCH₃ and not NaOCH₂CH₃?