Question 1

Consider the synthesis below: What is compound X?

Accepted Answer

A)  O=C(OEt)2 
B)  HCO2Et 
C)  EtO-CO-CO-OEt 
D)  CH3CO2Et 
E)  BrCH2CO2Et 
A)  O=C(OEt)2 
B)  HCO2Et 
C)  EtO-CO-CO-OEt 
D)  CH3CO2Et 
E)  BrCH2CO2Et

Question 2

Predict the product of 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 3

What would be the product of the following reaction?

Accepted Answer

A) 
  
B)  CH3CH=CHCO2CN 
C)  CH3CH=CHCN 
D) 
  
E) 
  
A) 
  
B)  CH3CH=CHCO2CN 
C)  CH3CH=CHCN 
D) 
  
E)

Question 4

Which of these combinations is not one which would result in the formation of essentially one Claisen condensation product when one compound is added slowly to the mixture of the other and the base employed?

Accepted Answer

A) 
HCO2Et + CH3CH2CO2Et 
B)  PhCO2Et + CH3CO2Et 
C)  (CO2Et)2 + PhCH2CO2Et 
D)  (CH3)3CCO2Et + CH3CO2Et 
E)  PhCH2CO2Et + CH3CO2Et 
A) 
HCO2Et + CH3CH2CO2Et 
B)  PhCO2Et + CH3CO2Et 
C)  (CO2Et)2 + PhCH2CO2Et 
D)  (CH3)3CCO2Et + CH3CO2Et 
E)  PhCH2CO2Et + CH3CO2Et

Question 5

What is the product of the Dieckmann-like condensation of this ketoester,

Accepted Answer

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

Question 6

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 7

What would be the major 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 8

What would be the major product,B,of 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 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 10

The aldol cyclization of   produces which of these?

Accepted Answer

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

Question 11

In the Claisen-Schmidt condensation of 1 mole of acetone with 2 moles 4-methyl benzaldehyde draw the possible products that form.

Accepted Answer

The answer of In the Claisen-Schmidt condensation of 1 mole...

Question 12

When   cyclizes in basic solution,which of these compounds will be formed?

Accepted Answer

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

Question 13

What would be the product,B,of the following reaction sequence?

Accepted Answer

A)  C6H5CH=CHCO2H 
B) 
  
C)  C6H5CH2CH2CO2H 
D) 
  
E) 
  
A)  C6H5CH=CHCO2H 
B) 
  
C)  C6H5CH2CH2CO2H 
D) 
  
E)

Question 14

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 15

What would be the product,C,of the following reaction sequence?

Accepted Answer

A)  (CH3)3CCH2CH2CH2OH 
B) 
  
C) 
  
D) 
  
E) 
  
A)  (CH3)3CCH2CH2CH2OH 
B) 
  
C) 
  
D) 
  
E)

Question 16

An intramolecular Claisen condensation is known as a _____________.

Accepted Answer

Dieckmann

Question 17

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 18

The retro-aldol reaction of   gives:

Accepted Answer

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

Question 19

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 20

What would be the major 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

Exam 19: Synthesis and Reactions of Beta-Dicarbonyl Compounds: More Chemistry of Enolate Ions

Consider the synthesis below: What is compound X?

Predict the product of the following reaction sequence.

What would be the product of the following reaction?

Which of these combinations is not one which would result in the formation of essentially one Claisen condensation product when one compound is added slowly to the mixture of the other and the base employed?

What is the product of the Dieckmann-like condensation of this ketoester,

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

What would be the major product of the following reaction?

What would be the major product,B,of the following reaction sequence?

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

The aldol cyclization of produces which of these?

In the Claisen-Schmidt condensation of 1 mole of acetone with 2 moles 4-methyl benzaldehyde draw the possible products that form.

When cyclizes in basic solution,which of these compounds will be formed?

What would be the product,B,of the following reaction sequence?

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

What would be the product,C,of the following reaction sequence?

An intramolecular Claisen condensation is known as a _____________.

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

The retro-aldol reaction of gives:

Predict the product from the following sequence:

What would be the major product of the following reaction?

Carbon Compounds and Chemical Bonds

Representative Carbon Compounds: Functional Groups, Intermolecular Forces, and Infrared Ir Spectroscopy

An Introduction to Organic Reactions: Acids and Bases

Alkanes: Nomenclature, Conformational Analysis, and an Introduction to Synthesis

Stereochemistry: Chiral Molecules

Ionic Reactions - Nucleophilic Substitution and Elimination Reactions of Alkyl Halides

Alkenes and Alkynes I: Properties and Synthesis, Elimination Reactions of Alkyl Halides

Alkenes and Alkynes Ii: Addition Reactions

Nuclear Magnetic Resonance and Mass Spectrometry: Tools for Structure Determination

Radical Reactions

Alcohols and Ethers

Alcohols From Carbonyl Compounds Oxidation-Reduction and Organometallic Compounds

Conjugated Unsaturated Systems

Aromatic Compounds

Reactions of Aromatic Compounds

Aldehydes and Ketones I Nucleophilic Addition to the Carbonyl Group

Aldehydes and Ketones Ii Aldol Reactions

Carboxylic Acids and Their Derivatives Nucleophilic Addition - Elimination at the Acyl Carbon

Amines

Phenols and Aryl Halides: Nucleophilic Aromatic Substitution

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

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