Question 1

Give the major product of the following reaction.

Accepted Answer

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

Question 2

Provide a detailed, stepwise mechanism for the formation of acetate and bromodiiodomethane from bromoacetone, hydroxide and iodine.

Accepted Answer

The answer of Provide a detailed, stepwise mechanism for the...

Question 3

Which of the following is a β-diester?

Accepted Answer

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

Question 4

List the following carbonyl compounds in order of decreasing pKa: 2,4-pentanedione, diethyl malonate, propanal, ethyl acetate.

Accepted Answer

ethyl acetate > prop

Question 5

Show how an enolate can add to a carbonyl.

Accepted Answer

The answer of Show how an enolate can add to...

Question 6

What two molecules were condensed in an aldol reaction to produce
(CH3)3CCH   CHCOCH3?

Accepted Answer

Question 7

Draw the most stable enol tautomer of the ketone shown below.

Accepted Answer

The answer of Draw the most stable enol tautomer of...

Question 8

What is the major organic product of the following reaction

Accepted Answer

A) CH3CH2Br 
B)    
C)    
D)    
E)    
A) CH3CH2Br 
B)    
C)    
D)    
E)

Question 9

What is the major organic 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 10

How many Hs in the compound below are replaced by Ds when it is shaken in D2O containing trace hydroxide?

Accepted Answer

A) 1 
B) 2 
C) 3 
D) 6 
E) 7 
A) 1 
B) 2 
C) 3 
D) 6 
E) 7

Question 11

Give the major product for the following reaction.

Accepted Answer

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

Question 12

Starting with cyclohexene and employing a Dieckmann cyclization show how the compound below can be prepared.

Accepted Answer

1) KMnO4, ^-OH, Δ 2) H

Question 13

A student proposed the following synthesis. Why did it fail?

Accepted Answer

A) The use of LDA results in the thermodynamic product instead of the desired kinetic product. 
B) LDA is insoluble in the THF solvent so the reaction is too slow to occur at a useful rate. 
C) LDA acts as a nucleophile instead of a base in its reaction with cyclohexanone. 
D) The tertiary bromide is too sterically hindered to be attacked by the enolate. 
E) Instead of 2-methyl-2-bromopentane, 2-bromo-3-methylpentane should have been used to anticipate a cationic rearrangement that would occur. 
A) The use of LDA results in the thermodynamic product instead of the desired kinetic product. 
B) LDA is insoluble in the THF solvent so the reaction is too slow to occur at a useful rate. 
C) LDA acts as a nucleophile instead of a base in its reaction with cyclohexanone. 
D) The tertiary bromide is too sterically hindered to be attacked by the enolate. 
E) Instead of 2-methyl-2-bromopentane, 2-bromo-3-methylpentane should have been used to anticipate a cationic rearrangement that would occur.

Question 14

Which is the major organic product from the following reaction?

Accepted Answer

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

Question 15

Rank the following compounds in order of increasing acidity of their a-Hs, least acidic to most acidic: CH3CH2CON(CH3)2, PhCOCH2CHO, CH3CH2CO2CH2CH3, and PhCOCH2CO2CH2CH3.

Accepted Answer

CH₃CH₂CON(CH₃)₂ < CH₃CH₂CO

Question 16

Provide the major organic product of the following.

Accepted Answer

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

Question 17

Propose a stepwise mechanism that would explain the following conversion:

Accepted Answer

The answer of Propose a stepwise mechanism that would explain...

Question 18

Give the major product for the reaction.

Accepted Answer

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

Question 19

When compared to the keto form, the enol form of which of the following compounds is most stable?

Accepted Answer

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

Question 20

What product results when malonic ester is treated with the following sequence of reagents:
1)NaOCH2CH3;
2)PhCH2Br;
3)H3O+, Δ?

Accepted Answer

Exam 18: Reactions at the Alpha Carbon of Carbonyl Compounds

Give the major product of the following reaction.

Provide a detailed, stepwise mechanism for the formation of acetate and bromodiiodomethane from bromoacetone, hydroxide and iodine.

Which of the following is a β-diester?

List the following carbonyl compounds in order of decreasing pKa: 2,4-pentanedione, diethyl malonate, propanal, ethyl acetate.

Show how an enolate can add to a carbonyl.

What two molecules were condensed in an aldol reaction to produce (CH3)3CCH CHCOCH3?

Draw the most stable enol tautomer of the ketone shown below.

What is the major organic product of the following reaction

What is the major organic product of the following reaction?

How many Hs in the compound below are replaced by Ds when it is shaken in D2O containing trace hydroxide?

Give the major product for the following reaction.

Starting with cyclohexene and employing a Dieckmann cyclization show how the compound below can be prepared.

A student proposed the following synthesis. Why did it fail?

Which is the major organic product from the following reaction?

Rank the following compounds in order of increasing acidity of their a-Hs, least acidic to most acidic: CH3CH2CON(CH3)2, PhCOCH2CHO, CH3CH2CO2CH2CH3, and PhCOCH2CO2CH2CH3.

Provide the major organic product of the following.

Propose a stepwise mechanism that would explain the following conversion:

Give the major product for the reaction.

When compared to the keto form, the enol form of which of the following compounds is most stable?

What product results when malonic ester is treated with the following sequence of reagents: 1)NaOCH2CH3; 2)PhCH2Br; 3)H3O+, Δ?

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

What two molecules were condensed in an aldol reaction to produce (CH₃)₃CCH CHCOCH₃?

How many Hs in the compound below are replaced by Ds when it is shaken in D₂O containing trace hydroxide?

Rank the following compounds in order of increasing acidity of their a-Hs, least acidic to most acidic: CH₃CH₂CON(CH₃)₂, PhCOCH₂CHO, CH₃CH₂CO₂CH₂CH₃, and PhCOCH₂CO₂CH₂CH₃.

What product results when malonic ester is treated with the following sequence of reagents: 1)NaOCH₂CH₃; 2)PhCH₂Br; 3)H₃O+, Δ?