Question 1

Which one of the following compounds does not undergo an aldol addition reaction in the presence of aqueous sodium hydroxide?

Accepted Answer

A)  butanal 
B)  2-methylbutanal 
C)  3-methylpentanal 
D)  2,2-dimethylbutanal 
E)  pentanal 
A)  butanal 
B)  2-methylbutanal 
C)  3-methylpentanal 
D)  2,2-dimethylbutanal 
E)  pentanal

Question 2

Predict the 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

Provide the reactants necessary to prepare the following compound using Robinson annulation.

Accepted Answer

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

Question 4

Provide the structure of the enol when 3,3,6-trimethyl-4-heptanone is treated with acid.

Accepted Answer

The answer of Provide the structure of the enol when...

Question 5

Predict the product(s) for the following reaction.

Accepted Answer

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

Question 6

Give the organic by-product in a haloform reaction.

Accepted Answer

The answer of Give the organic by-product in a haloform...

Question 7

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 8

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

Accepted Answer

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

Question 9

Predict the 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 10

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 11

How many gamma 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 12

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 13

Which of the following nucleophiles will undergo conjugate addition in a Michael reaction?

Accepted Answer

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

Question 14

Predict the product(s) for the following reaction.

Accepted Answer

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

Question 15

Which is the most acidic hydrogen in the following compound?

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 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 17

Predict the product(s) for the following reaction.

Accepted Answer

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

Question 18

Which is the most acidic hydrogen in the following compound?

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 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 20

Provide the reagents necessary to carry out the following conversion using a Stork enamine synthesis.

Accepted Answer

1. (CH₃)₂NH/

Exam 21: Alpha Carbon Chemistry: Enols and Enolates

Which one of the following compounds does not undergo an aldol addition reaction in the presence of aqueous sodium hydroxide?

Predict the product for the following reaction sequence.

Provide the reactants necessary to prepare the following compound using Robinson annulation.

Provide the structure of the enol when 3,3,6-trimethyl-4-heptanone is treated with acid.

Predict the product(s) for the following reaction.

Give the organic by-product in a haloform reaction.

Predict the product for the following reaction.

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

Predict the product for the following reaction sequence.

Predict the major product for the following reaction.

How many gamma hydrogens are in 2-pentanone?

Predict the product for the following reaction.

Which of the following nucleophiles will undergo conjugate addition in a Michael reaction?

Predict the product(s) for the following reaction.

Which is the most acidic hydrogen in the following compound?

Predict the major product for the following reaction.

Predict the product(s) for the following reaction.

Which is the most acidic hydrogen in the following compound?

Predict the major product for the following reaction.

Provide the reagents necessary to carry out the following conversion using a Stork enamine synthesis.

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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