Question 1

The b-hydroxy carbonyl product of an Aldol reaction is oftentimes not the final isolated product; what is the explanation for this result?

Accepted Answer

A) It undergoes elimination,since water is a good leaving group. 
B) The hydroxy group is oxidized to a carbonyl. 
C) The hydroxy group reacts with the carbonyl to form a ketal. 
D) Hydroxide is eliminated via an enolate intermediate. 
A) It undergoes elimination,since water is a good leaving group. 
B) The hydroxy group is oxidized to a carbonyl. 
C) The hydroxy group reacts with the carbonyl to form a ketal. 
D) Hydroxide is eliminated via an enolate intermediate. D

Question 2

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 B

Question 3

What is the product of the following Claisen reaction?

Accepted Answer

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

Question 4

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 5

What are the two starting materials for a Robinson annulation?

Accepted Answer

A) an a,b-Unsaturated carbonyl compound and an enolate 
B) a b-Ketoester and an enolate 
C) a 1,5-Dicarbonyl compound and an enolate 
D) a 1,3-Dicarbonyl compound and an enolate 
A) an a,b-Unsaturated carbonyl compound and an enolate 
B) a b-Ketoester and an enolate 
C) a 1,5-Dicarbonyl compound and an enolate 
D) a 1,3-Dicarbonyl compound and an enolate

Question 6

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 7

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.

Question 8

What product (including stereochemistry)is formed in the following intermolecular reaction?

Accepted Answer

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

Question 9

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 10

In the correct order,what are the three steps in the mechanism of an Aldol reaction?

Accepted Answer

A) Protonation,enolate formation,nucleophilic addition 
B) Enolate formation,protonation,nucleophilic addition 
C) Enolate formation,nucleophilic addition,protonation 
D) Nucleophilic addition,enolate formation,protonation 
A) Protonation,enolate formation,nucleophilic addition 
B) Enolate formation,protonation,nucleophilic addition 
C) Enolate formation,nucleophilic addition,protonation 
D) Nucleophilic addition,enolate formation,protonation

Question 11

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

Accepted Answer

A) When both carbonyl compounds have a hydrogens 
B) When both carbonyl compounds have no a hydrogens 
C) When one carbonyl compound has no a hydrogens 
D) When one carbonyl compound has no b hydrogens 
A) When both carbonyl compounds have a hydrogens 
B) When both carbonyl compounds have no a hydrogens 
C) When one carbonyl compound has no a hydrogens 
D) When one carbonyl compound has no b hydrogens

Question 12

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

Question 13

What is the name given to an Aldol reaction between two different carbonyl compounds?

Accepted Answer

A) Multiple Aldol reaction 
B) Crossed Aldol reaction 
C) Differential Aldol reaction 
D) Versatile Aldol reaction 
A) Multiple Aldol reaction 
B) Crossed Aldol reaction 
C) Differential Aldol reaction 
D) Versatile Aldol reaction

Question 14

What type of esters can undergo Claisen reactions?

Accepted Answer

A) All esters can undergo Claisen reactions. 
B) Only esters with two hydrogen atoms on the a carbon can undergo Claisen reactions. 
C) Only esters with three hydrogen atoms on the a carbon can undergo Claisen reactions. 
D) Only esters with two or three hydrogen atoms on the a carbon can undergo Claisen reactions. 
A) All esters can undergo Claisen reactions. 
B) Only esters with two hydrogen atoms on the a carbon can undergo Claisen reactions. 
C) Only esters with three hydrogen atoms on the a carbon can undergo Claisen reactions. 
D) Only esters with two or three hydrogen atoms on the a carbon can undergo Claisen reactions.

Question 15

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 16

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 17

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

Accepted Answer

A) a-Carbon 
B) b-Carbon 
C) Carbonyl carbon 
D) Carbonyl carbon and b-carbon 
A) a-Carbon 
B) b-Carbon 
C) Carbonyl carbon 
D) Carbonyl carbon and b-carbon

Question 18

Which is the unsaturated carbonyl compound formed by the dehydration of the following b-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 19

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

Question 20

What is the cyclic product formed in the intramolecular Aldol condensation when the following compound is treated with aqueous NaOH?

Accepted Answer

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

Exam 22: Carbonyl Condensation Reactions

The b-hydroxy carbonyl product of an Aldol reaction is oftentimes not the final isolated product; what is the explanation for this result?

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

What is the product of the following Claisen reaction?

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

What are the two starting materials for a Robinson annulation?

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

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

What product (including stereochemistry)is formed in the following intermolecular reaction?

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

In the correct order,what are the three steps in the mechanism of an Aldol reaction?

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

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

What is the name given to an Aldol reaction between two different carbonyl compounds?

What type of esters can undergo Claisen reactions?

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

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

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

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

What reaction type is an Aldol reaction?

What is the cyclic product formed in the intramolecular Aldol condensation when the following compound is treated with aqueous NaOH?

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 Related Compounds

Alkenes and Addition Reactions

Alkynes and Synthesis

Oxidation and Reduction

Radical Reactions

Conjugation,resonance,and Dienes

Benzene and Aromatic Compounds

Reactions of Aromatic Compounds

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones - Nucleophilic Addition

Carboxylic Acids and the Acidity of the O-H Bond

Carboxylic Acids and Their Derivatives Nucleophilic Acyl Substitution

Substitution Reactions of Carbonyl Compounds at the a Carbon

Amines

Carbon-Carbon Bond-Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Synthetic Polymers

Lipids

Spectroscopy A: Mass Spectrometry

Spectroscopy B: Infrared Spectroscopy

Spectroscopy C: Nuclear Magnetic Resonance Spectroscopy

Filters

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