Question 1

Which of the following compounds has the most stable enol tautomer?

Accepted Answer

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

Question 2

Provide the major organic product of the following.

Accepted Answer

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

Question 3

Give the major product for the following reaction.

Accepted Answer

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

Question 4

Which of the following could result from the dehydration of an aldol?

Accepted Answer

A) 4-methyl-3-penten-2-one 
B) 4-methyl-4-penten-2-one 
C) 4-methyl-5-hexen-2-one 
D) 4-methyl-4-hexen-2-one 
E) 3-methyl-4-penten-2-one 
A) 4-methyl-3-penten-2-one 
B) 4-methyl-4-penten-2-one 
C) 4-methyl-5-hexen-2-one 
D) 4-methyl-4-hexen-2-one 
E) 3-methyl-4-penten-2-one

Question 5

Which of the following compounds will react with methyl vinyl ketone in a Robinson annulation to generate the cyclic enone below?

Accepted Answer

A) 1-pentene 
B) cyclohexanone 
C) 2-pentanone 
D) pentanal 
E) none of the above 
A) 1-pentene 
B) cyclohexanone 
C) 2-pentanone 
D) pentanal 
E) none of the above

Question 6

Provide a synthesis of 2-ethylhexanol using butanal as the only source of carbon.

Accepted Answer

@#IMG-DLM&_TB1830_00 Depending on the co

Question 7

Which of the following statements describes the first step in the mechanism of the aldol condensation?

Accepted Answer

A) An alpha hydrogen is abstracted by the base to form an enolate anion. 
B) A nucleophilic base attacks the carbonyl carbon atom. 
C) The carbonyl oxygen is protonated by the base ion. 
D) The alpha hydrogen is abstracted by an acid to the enolate anion. 
E) The carbonyl oxygen of one aldehyde attacks the carbonyl carbon of another. 
A) An alpha hydrogen is abstracted by the base to form an enolate anion. 
B) A nucleophilic base attacks the carbonyl carbon atom. 
C) The carbonyl oxygen is protonated by the base ion. 
D) The alpha hydrogen is abstracted by an acid to the enolate anion. 
E) The carbonyl oxygen of one aldehyde attacks the carbonyl carbon of another.

Question 8

When the 1,7-diester CH3O2CCH2CH2CH(CH3)CH2CH2CO2CH3 is treated with sodium methoxide and the reaction mixture is subsequently neutralized with acid, what kind of compound is the major organic product?

Accepted Answer

A) an acyclic β-diketone 
B) an acyclic β-ketoacid 
C) an acyclic β-diester 
D) a cyclic β-ketoester 
E) a cyclic β-diketone 
A) an acyclic β-diketone 
B) an acyclic β-ketoacid 
C) an acyclic β-diester 
D) a cyclic β-ketoester 
E) a cyclic β-diketone

Question 9

Which compound has the lowest pKa?

Accepted Answer

A) (CH3CH2O2
C) 2CH2 
B) CH3CH2O2CCH2CHO 
C) CH3CH2COCH2CHO 
D) PhCOCH2COCH3 
E) (N
C) 2CH2 
A) (CH3CH2O2
C) 2CH2 
B) CH3CH2O2CCH2CHO 
C) CH3CH2COCH2CHO 
D) PhCOCH2COCH3 
E) (N
C) 2CH2

Question 10

What alkyl bromide should be used in the malonic ester synthesis of the following carboxylic acid?

Accepted Answer

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

Question 11

Which of the following aldehydes does not undergo an aldol addition when mixed with base?

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 structure of the major organic product which results when PhCO2CH2CH3 and CH3CH2CO2CH2CH3 are heated in the presence of sodium ethoxide and the compound generated is subsequently treated with cold, dilute acid.

Accepted Answer

Question 13

Provide a detailed, stepwise mechanism for the transformation shown below.

Accepted Answer

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

Question 14

Give the major product for the following reaction.

Accepted Answer

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

Question 15

What is the molecular formula of the major organic product of the following reaction sequence?

Accepted Answer

A) C7H12O 
B) C7H14O 
C) C11H19N 
D) C11H21N 
E) C11H23N 
A) C7H12O 
B) C7H14O 
C) C11H19N 
D) C11H21N 
E) C11H23N

Question 16

Which of the labeled hydrogen atoms in the following structure is the most acidic?

Accepted Answer

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

Question 17

Identify the major organic product of the following sequence.

Accepted Answer

A) 3-bromocyclohexanone 
B) 4-bromocyclohexanone 
C) 3-hydroxycyclohexanone 
D) 4-hydroxycyclohexanone 
E) 2-cyclohexenone 
A) 3-bromocyclohexanone 
B) 4-bromocyclohexanone 
C) 3-hydroxycyclohexanone 
D) 4-hydroxycyclohexanone 
E) 2-cyclohexenone

Question 18

Which of the following is the most stable enol form of 1,3-cyclohexanedione?

Accepted Answer

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

Question 19

Which of the following compounds will give a positive iodoform test?

Accepted Answer

A) propanal 
B) 2-pentanone 
C) 3-pentanone 
D) benzophenone 
E) cyclohexanone 
A) propanal 
B) 2-pentanone 
C) 3-pentanone 
D) benzophenone 
E) cyclohexanone

Question 20

Provide a detailed, stepwise mechanism for the base-catalyzed enolization of acetaldehyde.

Accepted Answer

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

Exam 18: Reactions at the Alpha Carbon of Carbonyl Compounds

Which of the following compounds has the most stable enol tautomer?

Provide the major organic product of the following.

Give the major product for the following reaction.

Which of the following could result from the dehydration of an aldol?

Which of the following compounds will react with methyl vinyl ketone in a Robinson annulation to generate the cyclic enone below?

Provide a synthesis of 2-ethylhexanol using butanal as the only source of carbon.

Which of the following statements describes the first step in the mechanism of the aldol condensation?

When the 1,7-diester CH3O2CCH2CH2CH(CH3)CH2CH2CO2CH3 is treated with sodium methoxide and the reaction mixture is subsequently neutralized with acid, what kind of compound is the major organic product?

Which compound has the lowest pKa?

What alkyl bromide should be used in the malonic ester synthesis of the following carboxylic acid?

Which of the following aldehydes does not undergo an aldol addition when mixed with base?

Provide the structure of the major organic product which results when PhCO2CH2CH3 and CH3CH2CO2CH2CH3 are heated in the presence of sodium ethoxide and the compound generated is subsequently treated with cold, dilute acid.

Provide a detailed, stepwise mechanism for the transformation shown below.

Give the major product for the following reaction.

What is the molecular formula of the major organic product of the following reaction sequence?

Which of the labeled hydrogen atoms in the following structure is the most acidic?

Identify the major organic product of the following sequence.

Which of the following is the most stable enol form of 1,3-cyclohexanedione?

Which of the following compounds will give a positive iodoform test?

Provide a detailed, stepwise mechanism for the base-catalyzed enolization of acetaldehyde.

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 the 1,7-diester CH₃O₂CCH₂CH₂CH(CH₃)CH₂CH₂CO₂CH₃ is treated with sodium methoxide and the reaction mixture is subsequently neutralized with acid, what kind of compound is the major organic product?

Provide the structure of the major organic product which results when PhCO₂CH₂CH₃ and CH₃CH₂CO₂CH₂CH₃ are heated in the presence of sodium ethoxide and the compound generated is subsequently treated with cold, dilute acid.