Question 1

Using 1-propanol as your only source of carbon, and using any other reagents as appropriate, write a complete stepwise synthesis for 3-hexanone.

Accepted Answer

@#IMG-DLM&_TB4454_00

Question 2

Provide 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 3

Which of the following statements is consistent with the mechanism for the nucleophilic addition of aldehydes/ketones under basic conditions?

Accepted Answer

A)  a proton transfer followed by a nucleophilic attack 
B)  a nucleophilic attack followed by a proton transfer 
C)  nucleophilic attack is the only step 
D)  proton transfer is not required 
A)  a proton transfer followed by a nucleophilic attack 
B)  a nucleophilic attack followed by a proton transfer 
C)  nucleophilic attack is the only step 
D)  proton transfer is not required

Question 4

Provide the reagents necessary for the following conversion.

Accepted Answer

A)  1. NaBH4/CH3OH
2) CH3CH2MgBr 
B)  CH3CH2MgBr/ether 
C)  1. H3O+
2) CH3CH2MgBr/ ether 
D)  1. CH3CH2MgBr/ ether
2) H3O+,$\Delta$ 
A)  1. NaBH4/CH3OH
2) CH3CH2MgBr 
B)  CH3CH2MgBr/ether 
C)  1. H3O+
2) CH3CH2MgBr/ ether 
D)  1. CH3CH2MgBr/ ether
2) H3O+,$\Delta$

Question 5

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 6

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 7

What is the structure for 5-hydroxy-2-phenyl-3-hexanone?

Accepted Answer

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

Question 8

Suggest a stepwise synthesis for 1-pentanol from butanal.

Accepted Answer

@#IMG-DLM&_TB4454_00

Question 9

Predict the product(s) for the following reaction.

Accepted Answer

The answer of Predict the product(s) for the following reaction....

Question 10

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 11

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 12

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 13

Provide the reactants that will form the following enamine.

Accepted Answer

The answer of Provide the reactants that will form the...

Question 14

What is the IUPAC name for the following compound?

Accepted Answer

A)  (S)-2-methyl-2-bromobutanone 
B)  (S)-2-bromo-2-methylcyclobutanone 
C)  (R)-2-bromo-2-methylcyclobutanone 
D)  (S)-1-bromo-1-methyl-2-cyclobutanone 
E)  (R)-1-bromo-1-methyl-2-cyclobutanone 
A)  (S)-2-methyl-2-bromobutanone 
B)  (S)-2-bromo-2-methylcyclobutanone 
C)  (R)-2-bromo-2-methylcyclobutanone 
D)  (S)-1-bromo-1-methyl-2-cyclobutanone 
E)  (R)-1-bromo-1-methyl-2-cyclobutanone

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 for the following reaction.

Accepted Answer

The answer of Predict the product for the following reaction....

Question 17

Suggest a stepwise synthesis for 5-methylhexanal from 3-methyl-1-bromobutane.

Accepted Answer

@#IMG-DLM&_TB4454_00

Question 18

Provide the reagents necessary to carry out the following conversion.

Accepted Answer

1. HOCH₂CH₂O

Question 19

Suggest a stepwise synthesis for the following.

Accepted Answer

@#IMG-DLM&_TB4454_00

Question 20

Predict the product, when 4-methyl-2-hexanone reacts with hydrazine in the presence of an acid catalyst.

Accepted Answer

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

Exam 19: Aldehydes and Ketones

Using 1-propanol as your only source of carbon, and using any other reagents as appropriate, write a complete stepwise synthesis for 3-hexanone.

Provide the product for the following reaction.

Which of the following statements is consistent with the mechanism for the nucleophilic addition of aldehydes/ketones under basic conditions?

Provide the reagents necessary for the following conversion.

Predict the product of the following reaction sequence,

Predict the product for the following reaction.

What is the structure for 5-hydroxy-2-phenyl-3-hexanone?

Suggest a stepwise synthesis for 1-pentanol from butanal.

Predict the product(s) for the following reaction.

What would be the product of the following reaction?

Predict the product of the following reaction sequence,

Predict the product for the following reaction sequence.

Provide the reactants that will form the following enamine.

What is the IUPAC name for the following compound?

What would be the product of the following reaction?

Predict the product for the following reaction.

Suggest a stepwise synthesis for 5-methylhexanal from 3-methyl-1-bromobutane.

Provide the reagents necessary to carry out the following conversion.

Suggest a stepwise synthesis for the following.

Predict the product, when 4-methyl-2-hexanone reacts with hydrazine in the presence of an acid catalyst.

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

Carboxylic Acids and Their Derivatives

Alpha Carbon Chemistry: Enols and Enolates

Amines

Introduction to Organometallic Compounds

Carbohydrates

Amino Acids, Peptides, and Proteins

Lipids

Synthetic Polymers

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