Question 1

Which is the thermodynamic enolate of 2-methylcyclohexanone?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) A) and B)
F) None of the above

Question 2

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

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) A) and D)
F) B) and D)

Question 3

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 IIIE) All of the above
F) B) and C)

Question 4

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

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) A) and C)
F) All of the above

Question 5

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 epimerE) A) and D)
F) A) and C)

Question 6

What is the missing reagent in the reaction below?
2/AcOH B) I2/KOH C) I2 D) KOH" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  Br2/AcOH
B)  I2/KOH
C)  I2
D)  KOHE) None of the above
F) All of the above

Question 7

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.E) B) and C)
F) A) and B)

Question 8

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

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) B) and D)
F) None of the above

Question 9

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

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) C) and D)
F) A) and B)

Question 10

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 stableE) A) and C)
F) C) and D)

Question 11

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.E) B) and D)
F) C) and D)

Question 12

What is the product of the following reaction?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) B) and C)
F) None of the above

Question 13

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.E) B) and C)
F) A) and B)

Question 14

What is the starting material for the following reaction?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) None of the above
F) A) and D)

Question 15

Which is the most acidic proton in the following compound?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) B) and D)
F) A) and B) C

Question 16

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.E) None of the above
F) A) and D)

Question 17

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 hydrideE) None of the above
F) B) and C)

Question 18

Which is the most acidic proton in the following compound?

Accepted Answer

A)  I
B)  II
C)  III
D)  IVE) None of the above
F) B) and C) A

Question 19

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.E) A) and B)
F) A) and C)

Question 20

What is the missing reagent for the following reaction?
2/HOAc B) Br2/KOH C) Cl2/FeCl3 D) Br2/FeBr3" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  Br2/HOAc
B)  Br2/KOH
C)  Cl2/FeCl3
D)  Br2/FeBr3E) None of the above
F) B) and D) A

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

Which is the thermodynamic enolate of 2-methylcyclohexanone?

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

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

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

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

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What is the missing reagent in the reaction below?

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

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

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

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Which is the more stable form of acetophenone?

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

Correct AnswerverifiedShow Answer

What is the product of the following reaction?

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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:

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What is the starting material for the following reaction?

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Which is the most acidic proton in the following compound?

Correct AnswerverifiedC

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?

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

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Which is the most acidic proton in the following compound?

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

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What is the missing reagent for the following reaction?

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C

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A

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A