Question 1

How many alpha hydrogens are in 2-pentanone?

Accepted Answer

A)  1 
B)  2 
C)  3 
D)  4 
E)  5 
A)  1 
B)  2 
C)  3 
D)  4 
E)  5

Question 2

Predict the final product for 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

Which of the following ketones will give a positive haloform test?

Accepted Answer

A)  3-heptanone 
B)  3-hexanone 
C)  cyclohexanone 
D)  2-pentanone 
E)  2-methyl-3-hexanone 
A)  3-heptanone 
B)  3-hexanone 
C)  cyclohexanone 
D)  2-pentanone 
E)  2-methyl-3-hexanone

Question 4

Predict the major product for the following reaction.

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  none of these 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  none of these

Question 5

Explain why the following equilibrium favors the enol tautomer.

Accepted Answer

The enol tautomer is

Question 6

Arrange the following indicated hydrogens in decreasing order (most to least) of acidity.

Accepted Answer

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

Question 7

Which of the following is a keto-enol tautomeric pair?

Accepted Answer

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

Question 8

Predict the product for 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

Provide the reagents necessary to carry out the following conversion.

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  all of them 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  all of them

Question 10

Predict the product for 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

Predict the major product for 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 12

Provide the reactant(s) that would give the following possible aldol condensation product.

Accepted Answer

The answer of Provide the reactant(s) that would give the...

Question 13

Which one of the following is not a possible product when a crossed aldol addition reaction is carried out with ethanal and butanal as reactants?

Accepted Answer

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

Question 14

Which of the following ketones cannot be prepared using an acetoacetic ester synthesis?

Accepted Answer

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

Question 15

Predict the major product for 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

Provide the reactant(s) that will yield the following Claisen condensation product.

Accepted Answer

The answer of Provide the reactant(s) that will yield the...

Question 17

Give the name of the reaction in which a carboxylic acid can undergo alpha halogenation.

Accepted Answer

Hell-Volha

Question 18

Which one of the following indicated hydrogens is most acidic?

Accepted Answer

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

Question 19

Predict the product for 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 20

Provide the reactants that would give the following aldol condensation product.

Accepted Answer

A)  I 
B)  II 
C)  III 
D)  IV 
E)  none of these 
A)  I 
B)  II 
C)  III 
D)  IV 
E)  none of these

Exam 21: Alpha Carbon Chemistry: Enols and Enolates

How many alpha hydrogens are in 2-pentanone?

Predict the final product for the following reaction sequence.

Which of the following ketones will give a positive haloform test?

Predict the major product for the following reaction.

Explain why the following equilibrium favors the enol tautomer.

Arrange the following indicated hydrogens in decreasing order (most to least) of acidity.

Which of the following is a keto-enol tautomeric pair?

Predict the product for the following reaction.

Provide the reagents necessary to carry out the following conversion.

Predict the product for the following reaction.

Predict the major product for the following reaction.

Provide the reactant(s) that would give the following possible aldol condensation product.

Which one of the following is not a possible product when a crossed aldol addition reaction is carried out with ethanal and butanal as reactants?

Which of the following ketones cannot be prepared using an acetoacetic ester synthesis?

Predict the major product for the following reaction.

Provide the reactant(s) that will yield the following Claisen condensation product.

Give the name of the reaction in which a carboxylic acid can undergo alpha halogenation.

Which one of the following indicated hydrogens is most acidic?

Predict the product for the following reaction.

Provide the reactants that would give the following aldol condensation product.

A Review of General Chemistry: Electrons, Bonds, and Molecular Properties

Molecular Representations

Acids and Bases

Alkanes and Cycloalkanes

Stereoisomerism

Chemical Reactivity and Mechanisms

Alkyl Halides: Nucleophilic Substitution and Elimination Reactions

Addition Reactions of Alkenes

Alkynes

Radical Reactions

Synthesis

Alcohols and Phenols

Ethers and Epoxides; Thiols and Sulfides

Infrared Spectroscopy and Mass Spectrometry

Nuclear Magnetic Resonance Spectroscopy

Conjugated Pi Systems and Pericyclic Reactions

Aromatic Compounds

Aromatic Substitution Reactions

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Amines

Introduction to Organometallic Compounds

Carbohydrates

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

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