Question 1

Provide the sequence of steps necessary to synthesize the compound shown below from cyclohexene.

Accepted Answer

1) O₃ 2) S(

Question 2

Give the major product for the following reaction.

Accepted Answer

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

Question 3

The Hell-Volhard-Zelinsky reaction involves ________.

Accepted Answer

A) the α-bromination of carboxylic acids 
B) the α-bromination of ketones 
C) the bromination of alcohols 
D) the oxidation of aldehydes to acids 
E) none of the above 
A) the α-bromination of carboxylic acids 
B) the α-bromination of ketones 
C) the bromination of alcohols 
D) the oxidation of aldehydes to acids 
E) none of the above

Question 4

Explain why the following acid cannot be prepared by the malonic ester synthesis:

Accepted Answer

Since bromobenzene is needed to prepare

Question 5

Give the major product for the following reaction.

Accepted Answer

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

Question 6

Which of the following keto-enol tautomers is more stable? Explain.

Accepted Answer

The enol form is more stable t

Question 7

What is the major organic product from 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

Give the major product for the following reaction.

Accepted Answer

The answer of Give the major product for the following...

Question 9

Provide the major organic product(s)of the reaction shown below.

Accepted Answer

The answer of Provide the major organic product(s)of the reaction...

Question 10

In the Michael reaction, addition to the α, β-unsaturated carbonyl occurs in a ________.

Accepted Answer

A) 1,2-fashion 
B) 1,3-fashion 
C) 1,4-fashion 
D) 1,5-fashion 
E) Diels-Alder reaction 
A) 1,2-fashion 
B) 1,3-fashion 
C) 1,4-fashion 
D) 1,5-fashion 
E) Diels-Alder reaction

Question 11

Why is the pKa of acetone 20 while that of ethane is 50? Explain the origin for this difference in acidity.

Accepted Answer

When a proton is removed from ethane, th

Question 12

What product is formed in the mixed Claisen condensation between methyl benzoate and cyclohexanone?

Accepted Answer

The answer of What product is formed in the mixed...

Question 13

Give the major product for the following reaction.

Accepted Answer

The answer of Give the major product for the following...

Question 14

Provide the major organic product(s)of the reaction shown below.

Accepted Answer

The answer of Provide the major organic product(s)of the reaction...

Question 15

Provide the major organic product of the following reaction.

Accepted Answer

The answer of Provide the major organic product of the...

Question 16

When compound X is heated, PhCOCH(CH3)2 and CO2 are produced. Offer a structure for compound X.

Accepted Answer

Question 17

Which of the following reagents will quantitatively convert an enolizable ketone to its enolate salt?

Accepted Answer

A) lithium hydroxide 
B) lithium diisopropylamide 
C) methyllithium 
D) diethylamine 
E) pyridine 
A) lithium hydroxide 
B) lithium diisopropylamide 
C) methyllithium 
D) diethylamine 
E) pyridine

Question 18

How would you accomplish the following conversion?

Accepted Answer

A) "H+/H2O; HC   N" 
B) "-OH/NaC   N" 
C) "Br2/H+, H2O; NaC   N" 
D) "HBr; NaC   N" 
E) "LiAlH4; HC   N; KMnO4" 
A) "H+/H2O; HC   N" 
B) "-OH/NaC   N" 
C) "Br2/H+, H2O; NaC   N" 
D) "HBr; NaC   N" 
E) "LiAlH4; HC   N; KMnO4"

Question 19

What materials are needed to prepare the following product?

Accepted Answer

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

Question 20

Give the major product for the following reaction.

Accepted Answer

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

Exam 18: Reactions at the Alpha Carbon of Carbonyl Compounds

Provide the sequence of steps necessary to synthesize the compound shown below from cyclohexene.

Give the major product for the following reaction.

The Hell-Volhard-Zelinsky reaction involves ________.

Explain why the following acid cannot be prepared by the malonic ester synthesis:

Give the major product for the following reaction.

Which of the following keto-enol tautomers is more stable? Explain.

What is the major organic product from the following reaction?

Give the major product for the following reaction.

Provide the major organic product(s)of the reaction shown below.

In the Michael reaction, addition to the α, β-unsaturated carbonyl occurs in a ________.

Why is the pKa of acetone 20 while that of ethane is 50? Explain the origin for this difference in acidity.

What product is formed in the mixed Claisen condensation between methyl benzoate and cyclohexanone?

Give the major product for the following reaction.

Provide the major organic product(s)of the reaction shown below.

Provide the major organic product of the following reaction.

When compound X is heated, PhCOCH(CH3)2 and CO2 are produced. Offer a structure for compound X.

Which of the following reagents will quantitatively convert an enolizable ketone to its enolate salt?

How would you accomplish the following conversion?

What materials are needed to prepare the following product?

Give the major product for the following reaction.

Remembering General Chemistry: Electronic Structure and Bonding

Acids and Bases: Central to Understanding Organic Chemistry

An Introduction to Organic Compounds

Isomers: the Arrangement of Atoms in Space

Alkenes Thermodynamics and Kinetics

Reactions of Alkenes

Reactions of Alkynes Introduction to Multistep Synthesis

Electron Delocalization, Resonance, and Aromaticity More About Molecular Orbital Theory

Substitution Reactions of Alkyl Halides

Elimination Reactions of Alkyl Halides Competition Between Substitution and Elimination

Reactions of Alcohols, Ethers, Epoxides, and Sulfur-Containing Compounds

Organometallic Compounds

Reactions of Alkanes, Radicals

Mass Spectrometry, Infrared Spectroscopy, and Uvvis Spectroscopy

Nmr Spectroscopy

Reactions of Carboxylic Acids and Carboxylic Acid Derivatives

Reactions of Aldehydes and Ketones

Reactions of Benzene and Substituted Benzenes

More About Amines Heterocylic Compounds

Carbohydrates

Amino Acids, Peptides, and Proteins

Catalysis

The Organic Mechanisms of the Coenzymes

The Chemistry of Metabolism

Nucleosides, Nucleotides, and Nucleic Acids

Synthetic Polymers

Pericyclic Reactions

Filters

When compound X is heated, PhCOCH(CH₃)₂ and CO₂ are produced. Offer a structure for compound X.