Question 1

Which reagents would you use to synthesize this compound by an aldol condensation?

Accepted Answer

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

Question 2

What is the final product of the following reaction sequence? Give structural details of all significant intermediates.

Accepted Answer

The answer of What is the final product of the...

Question 3

What is the expected product from the following reaction sequence?

Accepted Answer

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

Question 4

What is the expected product from the following reaction sequence?

Accepted Answer

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

Question 5

The Claisen condensation produces which of these?

Accepted Answer

A) An $\alpha$-keto ester 
B) A $\beta$-keto ester 
C) A $\beta$-hydroxy ester 
D) A $\beta$-hydroxyaldehyde 
E) A $\beta$-diketone 
A) An $\alpha$-keto ester 
B) A $\beta$-keto ester 
C) A $\beta$-hydroxy ester 
D) A $\beta$-hydroxyaldehyde 
E) A $\beta$-diketone

Question 6

Cyclization reactions,such as the Dieckmann condensation,are best carried out using fairly dilute solutions of the compound to be cyclized.Why is this so?

Accepted Answer

A) It then is possible to use less base. 
B) The reagents generally are expensive. 
C) A smaller amount of the compound to be cyclized can be used. 
D) Intermolecular condensation is minimized at low concentration. 
E) The concentration factor is unimportant. 
A) It then is possible to use less base. 
B) The reagents generally are expensive. 
C) A smaller amount of the compound to be cyclized can be used. 
D) Intermolecular condensation is minimized at low concentration. 
E) The concentration factor is unimportant.

Question 7

Why is CH3ONa not used in the Claisen condensation of ethyl acetate?

Accepted Answer

A) CH3O- is a weaker base than the CH3CH2O- which is used. 
B) CH3O-Na+ is more difficult to prepare than CH3CH2O-Na+. 
C) CH3O- would abstract a proton from the ethyl group of the ester. 
D) Use of CH3O-Na+ would result in transesterification. 
E) CH3O-Na+ can be used as well as CH3CH2O-Na+. 
A) CH3O- is a weaker base than the CH3CH2O- which is used. 
B) CH3O-Na+ is more difficult to prepare than CH3CH2O-Na+. 
C) CH3O- would abstract a proton from the ethyl group of the ester. 
D) Use of CH3O-Na+ would result in transesterification. 
E) CH3O-Na+ can be used as well as CH3CH2O-Na+.

Question 8

What is the expected product from the following reaction sequence?

Accepted Answer

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

Question 9

What would be the product of the following sequence?

Accepted Answer

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

Question 10

Which reagents would you use to synthesize this compound by an aldol condensation?

Accepted Answer

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

Question 11

What would be the product of the following sequence?

Accepted Answer

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

Question 12

When planning a reaction with an ester and an alkoxide ion,it is important to use an alkoxide that has the same alkyl group as the ester in order to avoid ___.

Accepted Answer

The answer of When planning a reaction with an ester...

Question 13

What is the product of the following reaction?

Accepted Answer

The answer of What is the product of the following...

Question 14

What is the product of the reaction sequence:

Accepted Answer

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

Question 15

What would be the product of the following reaction?

Accepted Answer

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

Question 16

Predict the product from the following sequence:

Accepted Answer

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

Question 17

What product results from the intramolecular aldol reaction of 2,5-hexanedione?

Accepted Answer

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

Question 18

Predict what is likely to happen when ethyl 6-oxooctanoate is treated with NaOEt,followed by acid work-up.

Accepted Answer

A cyclization similar to Dieck

Question 19

Which of these compounds cannot self-condense in the presence of dilute aqueous alkali?

Accepted Answer

A) 3-(4-Nitrophenyl)propanal 
B) 2-Methyl-3-pentanone 
C) 2-(4-Nitrophenyl)propanal 
D) 3-(4-Nitrophenyl)-2-butanone 
E) All of these compounds can self-condense. 
A) 3-(4-Nitrophenyl)propanal 
B) 2-Methyl-3-pentanone 
C) 2-(4-Nitrophenyl)propanal 
D) 3-(4-Nitrophenyl)-2-butanone 
E) All of these compounds can self-condense.

Question 20

What is the product of the Dieckmann condensation of this diester,

Accepted Answer

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

Exam 19: Condensation and Conjugate Addition Reactions of Carbonyl Compounds

Which reagents would you use to synthesize this compound by an aldol condensation?

What is the final product of the following reaction sequence? Give structural details of all significant intermediates.

What is the expected product from the following reaction sequence?

What is the expected product from the following reaction sequence?

The Claisen condensation produces which of these?

Cyclization reactions,such as the Dieckmann condensation,are best carried out using fairly dilute solutions of the compound to be cyclized.Why is this so?

Why is CH3ONa not used in the Claisen condensation of ethyl acetate?

What is the expected product from the following reaction sequence?

What would be the product of the following sequence?

Which reagents would you use to synthesize this compound by an aldol condensation?

What would be the product of the following sequence?

When planning a reaction with an ester and an alkoxide ion,it is important to use an alkoxide that has the same alkyl group as the ester in order to avoid ___.

What is the product of the following reaction?

What is the product of the reaction sequence:

What would be the product of the following reaction?

Predict the product from the following sequence:

What product results from the intramolecular aldol reaction of 2,5-hexanedione?

Predict what is likely to happen when ethyl 6-oxooctanoate is treated with NaOEt,followed by acid work-up.

Which of these compounds cannot self-condense in the presence of dilute aqueous alkali?

What is the product of the Dieckmann condensation of this diester,

The Basics

Families of Carbon

Acids and Bases

Nomenclature and Conformations of Alkanes and Cycloalkanes

Stereochemistry

Nucleophilic Reactions

Alkenes and Alkynes I

Alkenes and Alkynes II

Nuclear Magnetic Resonance and Mass Spectrometry

Radical Reactions

Alcohols and Ethers

Alcohols From Carbonyl Compounds

Conjugated Unsaturated Systems

Aromatic Compounds

Reactions of Aromatic Compounds

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Reactions at the Α Carbon of Carbonyl Compounds

Amines

Transition Metal Complexes

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

Why is CH₃ONa not used in the Claisen condensation of ethyl acetate?