Question 1

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 2

The interconversion of the keto and enol forms of a carbonyl compound is called ___.

Accepted Answer

The answer of The interconversion of the keto and enol...

Question 3

What would be the major 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 4

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 5

What is the product,L,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 6

Malonic ester (diethyl malonate)is treated successively with sodium ethoxide (1 eq.),1-bromopentane,potassium tert-butoxide,iodomethane,hot aqueous NaOH,HCl,and heat.What is the final product?

Accepted Answer

A) 2-Methylheptanoic acid 
B) 3-Methylhexanoic acid 
C) 3-Methylpentanoic acid 
D) 2-Methylpentanoic acid 
E) Ethyl 2-methylheptanoate 
A) 2-Methylheptanoic acid 
B) 3-Methylhexanoic acid 
C) 3-Methylpentanoic acid 
D) 2-Methylpentanoic acid 
E) Ethyl 2-methylheptanoate

Question 7

Which of the following could be used to synthesize the following substance in good yield?

Accepted Answer

A) Cyclohexanone,ClCH2COOH,AlCl3,heat 
B) Cyclohexanone,pyrrolidine,HA,(-H2O); then BrCH2COOC2H5; then OH-,H2O,heat; then H3O+ 
C) Cyclohexylacetic acid,KMnO4,OH-,heat; then H3O+ 
D) Two of these choices. 
E) All of these choices. 
A) Cyclohexanone,ClCH2COOH,AlCl3,heat 
B) Cyclohexanone,pyrrolidine,HA,(-H2O); then BrCH2COOC2H5; then OH-,H2O,heat; then H3O+ 
C) Cyclohexylacetic acid,KMnO4,OH-,heat; then H3O+ 
D) Two of these choices. 
E) All of these choices.

Question 8

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 9

Which reagent would best serve as the basis for a simple chemical test to distinguish between 2-pentanone and 3-pentanone?

Accepted Answer

A) NaOI (I2 in NaOH) 
B) Br2/CCl4 
C) CrO3/H2SO4 
D) NaHCO3/H2O 
E) Ag(NH3)2+ 
A) NaOI (I2 in NaOH) 
B) Br2/CCl4 
C) CrO3/H2SO4 
D) NaHCO3/H2O 
E) Ag(NH3)2+

Question 10

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 11

Which of the compounds listed below is more acidic than 2-pentanol?

Accepted Answer

A) Ethyl 3-oxopentanoate 
B) 2-Pentanone 
C) Pentanal 
D) All of these choices. 
E) Two of these choices. 
A) Ethyl 3-oxopentanoate 
B) 2-Pentanone 
C) Pentanal 
D) All of these choices. 
E) Two of these choices.

Question 12

What would be the major 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 13

What is the product,L,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 14

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 15

Considering only the highlighted hydrogens,list the following compounds in order of increasing acidity:

Accepted Answer

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

Question 16

Which of the compounds listed below is more acidic than 1-butanol?

Accepted Answer

A) Ethyl 2-oxocyclohexanecarboxylate 
B) 2-Butanone 
C) Ethyl pentanoate 
D) All of these choices. 
E) Two of these choices. 
A) Ethyl 2-oxocyclohexanecarboxylate 
B) 2-Butanone 
C) Ethyl pentanoate 
D) All of these choices. 
E) Two of these choices.

Question 17

Which of the following statements is true of the enamine,

Accepted Answer

A) The enamine can be made from cyclohexanone + pyrrolidine. 
B) It has another resonance structure :   
C) It can be acylated at the $\infty$-carbon of the original carbonyl compound. 
D) It can be alkylated. 
E) All of these choices are true. 
A) The enamine can be made from cyclohexanone + pyrrolidine. 
B) It has another resonance structure :   
C) It can be acylated at the $\infty$-carbon of the original carbonyl compound. 
D) It can be alkylated. 
E) All of these choices are true.

Question 18

Which of these amines is/are used with aldehydes and ketones to form enamines?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) Both I and II 
A) I 
B) II 
C) III 
D) IV 
E) Both I and II

Question 19

Simple enols are less stable than the tautomeric keto forms because:

Accepted Answer

A) severe angle strain exists in the enol forms. 
B) fewer atoms are coplanar in the keto form. 
C) the enol cannot be chiral. 
D) the C-C $\pi$ bond is weaker than the C-O $\pi$ bond. 
E) Actually,simple enols are the more stable. 
A) severe angle strain exists in the enol forms. 
B) fewer atoms are coplanar in the keto form. 
C) the enol cannot be chiral. 
D) the C-C $\pi$ bond is weaker than the C-O $\pi$ bond. 
E) Actually,simple enols are the more stable.

Question 20

Which of these amines is/are used with aldehydes and ketones to form enamines?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) I,II,and II 
A) I 
B) II 
C) III 
D) IV 
E) I,II,and II

Exam 18: Reactions at the Α Carbon of Carbonyl Compounds

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

The interconversion of the keto and enol forms of a carbonyl compound is called ___.

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

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

What is the product,L,of the following reaction sequence?

Malonic ester (diethyl malonate)is treated successively with sodium ethoxide (1 eq.),1-bromopentane,potassium tert-butoxide,iodomethane,hot aqueous NaOH,HCl,and heat.What is the final product?

Which of the following could be used to synthesize the following substance in good yield?

What would be the major product of the following reaction?

Which reagent would best serve as the basis for a simple chemical test to distinguish between 2-pentanone and 3-pentanone?

What would be the major product of the following reaction?

Which of the compounds listed below is more acidic than 2-pentanol?

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

What is the product,L,of the following reaction sequence?

What would be the major product of the following reaction?

Considering only the highlighted hydrogens,list the following compounds in order of increasing acidity:

Which of the compounds listed below is more acidic than 1-butanol?

Which of the following statements is true of the enamine,

Which of these amines is/are used with aldehydes and ketones to form enamines?

Simple enols are less stable than the tautomeric keto forms because:

Which of these amines is/are used with aldehydes and ketones to form enamines?

The Basics

Families of Carbon

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Nomenclature and Conformations of Alkanes and Cycloalkanes

Stereochemistry

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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

Condensation and Conjugate Addition Reactions of Carbonyl Compounds

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Transition Metal Complexes

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