Question 1

Which is the most acidic proton in the following compound?

Accepted Answer

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

Question 2

What is the missing reagent for the following reaction?

Accepted Answer

A) Br2/HOAc 
B) Br2/KOH 
C) Cl2/FeCl3 
D) Br2/FeBr3 
A) Br2/HOAc 
B) Br2/KOH 
C) Cl2/FeCl3 
D) Br2/FeBr3 A

Question 3

Which is the most acidic proton in the following compound?

Accepted Answer

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

Question 4

What is the starting material for the following reaction?

Accepted Answer

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

Question 5

What is the structure of X, product of the following reaction?

Accepted Answer

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

Question 6

It has been found that b-dicarbonyl compounds have a greater concentration of the enol form over the keto form.This can be explained by:

Accepted Answer

A) The C=C of the enol is conjugated with the carbonyl group. 
B) The -OH of the enol can hydrogen bond to the oxygen of the nearby carbonyl group. 
C) Both A and B above are true. 
D) None of the choices are true. 
A) The C=C of the enol is conjugated with the carbonyl group. 
B) The -OH of the enol can hydrogen bond to the oxygen of the nearby carbonyl group. 
C) Both A and B above are true. 
D) None of the choices are true.

Question 7

A simple chemical test to distinguish between acetone and 3-pentanone would be the reaction of the compounds with

Accepted Answer

A) bromine with acetic acid. 
B) bromine and aqueous hydroxide ion. 
C) THF, LDA at -78 °C followed by reaction with bromine. 
D) base and methyl bromide. 
A) bromine with acetic acid. 
B) bromine and aqueous hydroxide ion. 
C) THF, LDA at -78 °C followed by reaction with bromine. 
D) base and methyl bromide.

Question 8

If you want to form a kinetic enolate, you want to:

Accepted Answer

A) Use a strong, non-nucleophilic base such as LDA. 
B) Use a protic solvent. 
C) Use a low temperature. 
D) Both use a strong, non-nucleophilic base such as LDA and use a low temperature. 
A) Use a strong, non-nucleophilic base such as LDA. 
B) Use a protic solvent. 
C) Use a low temperature. 
D) Both use a strong, non-nucleophilic base such as LDA and use a low temperature.

Question 9

Which is the thermodynamic enolate of 2-methylcyclohexanone?

Accepted Answer

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

Question 10

What is (are) the product(s) of the following reaction?

Accepted Answer

A) Only I 
B) Only II 
C) Only III 
D) Only I and III 
A) Only I 
B) Only II 
C) Only III 
D) Only I and III

Question 11

Which of the following compounds would undergo racemization in the presence of a base?

Accepted Answer

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

Question 12

What is the starting material required to accomplish the following transformation?

Accepted Answer

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

Question 13

What is the product of the following reaction?

Accepted Answer

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

Question 14

Which of the following is the intermediate for halogenation of ketones under acidic conditions?

Accepted Answer

A) An enolate 
B) An enol 
C) A tautomer 
D) An epimer 
A) An enolate 
B) An enol 
C) A tautomer 
D) An epimer

Question 15

If you want to form a thermodynamic enolate, you want to:

Accepted Answer

A) Keep the reaction as cold as possible. 
B) Use an aprotic solvent such as THF. 
C) Use a protic solvent such as ethanol. 
D) Use a carboxylic acid. 
A) Keep the reaction as cold as possible. 
B) Use an aprotic solvent such as THF. 
C) Use a protic solvent such as ethanol. 
D) Use a carboxylic acid.

Question 16

Which of the following is an enol form of the following compound?

Accepted Answer

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

Question 17

Which is the more stable form of acetophenone?

Accepted Answer

A) Only I 
B) Only II 
C) Only III 
D) I and II are equally stable 
A) Only I 
B) Only II 
C) Only III 
D) I and II are equally stable

Question 18

For most compounds with a single keto group in the molecule, equilibrium favors the keto form over the enol form of the compound.This is due largely to what?

Accepted Answer

A) The C=O bond is much stronger than the C=C bond. 
B) The C=C bond is much stronger than the C=O bond. 
C) The keto form can undergo intramolecular hydrogen bonding. 
D) The enol form can undergo intramolecular hydrogen bonding. 
A) The C=O bond is much stronger than the C=C bond. 
B) The C=C bond is much stronger than the C=O bond. 
C) The keto form can undergo intramolecular hydrogen bonding. 
D) The enol form can undergo intramolecular hydrogen bonding.

Question 19

What is the missing reagent in the reaction below?

Accepted Answer

A) Br2/AcOH 
B) I2/KOH 
C) I2 
D) KOH 
A) Br2/AcOH 
B) I2/KOH 
C) I2 
D) KOH

Question 20

Which of the following bases will completely convert 1,4-cyclohexandione into an enolate?

Accepted Answer

A) Sodium hydroxide 
B) Sodium methoxide 
C) Sodium tert-butoxide 
D) Sodium hydride 
A) Sodium hydroxide 
B) Sodium methoxide 
C) Sodium tert-butoxide 
D) Sodium hydride

Exam 23: Substitution Reactions of Carbonyl Compounds at the Alpha-Carbon

Which is the most acidic proton in the following compound?

What is the missing reagent for the following reaction?

Which is the most acidic proton in the following compound?

What is the starting material for the following reaction?

What is the structure of X, product of the following reaction?

It has been found that b-dicarbonyl compounds have a greater concentration of the enol form over the keto form.This can be explained by:

A simple chemical test to distinguish between acetone and 3-pentanone would be the reaction of the compounds with

If you want to form a kinetic enolate, you want to:

Which is the thermodynamic enolate of 2-methylcyclohexanone?

What is (are) the product(s) of the following reaction?

Which of the following compounds would undergo racemization in the presence of a base?

What is the starting material required to accomplish the following transformation?

What is the product of the following reaction?

Which of the following is the intermediate for halogenation of ketones under acidic conditions?

If you want to form a thermodynamic enolate, you want to:

Which of the following is an enol form of the following compound?

Which is the more stable form of acetophenone?

For most compounds with a single keto group in the molecule, equilibrium favors the keto form over the enol form of the compound.This is due largely to what?

What is the missing reagent in the reaction below?

Which of the following bases will completely convert 1,4-cyclohexandione into an enolate?

Structure and Bonding

Acids and Bases

Introduction to Organic Molecules and Functional Groups

Alkanes

Stereochemistry

Understanding Organic Reactions

Alkyl Halides and Nucleophilic Substitution

Alkyl Halides and Elimination Reactions

Alcohols, Ethers, and Related Compounds

Alkenes

Alkynes

Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Radical Reactions

Conjugation, Resonance, and Dienes

Benzene and Aromatic Compounds

Reactions of Aromatic Compounds

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry;

Aldehydes and Ketones Nucleophilic Addition

Carboxylic Acids and Derivatives

Carbonyl Condensation Reactions

Amines

Carbon-Carbon Bond Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Synthetic Polymers

Lipids

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