Question 1

What is the major organic product obtained from the following sequence of reactions?

Accepted Answer

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

Question 2

What is the product of the following reaction?

Accepted Answer

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

Question 3

What is the structure of 3-methylcyclohexanone?

Accepted Answer

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

Question 4

Name the following aldehyde.

Accepted Answer

A)   1-methylcyclopentanal
B)   2-methylcyclopentanal
C)   2-methylcyclopentanecarbaldehyde
D)   1-methylcyclopentanylcarbaldehydeE) None of the above
F) B) and C)

Question 5

What sequence of reactions is required for the following transformation? 3P, [2] acetone C)  [1] Ph3P, [2] KOtBu, [3] acetone D)  acetone, heat" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   [1] NaOMe, [2] acetone
B)   [1] Ph3P, [2] acetone
C)   [1] Ph3P, [2] KOtBu, [3] acetone
D)   acetone, heatE) All of the above
F) A) and B)

Question 6

Why can't you use acidic conditions (such as aqueous hydrochloric acid)  for the addition of a Grignard reagent to a ketone?

Accepted Answer

A)   Because the Grignard reagent will react with the acid and be quenched.
B)   Because the ketone will be protonated and thus unreactive.
C)   Because the ketone will form an unreactive enol.
D)   Because the Grignard reagent won't dissolve in aqueous solutions.E) B) and C)
F) C) and D)

Question 7

Which of the following oxidants would work for the following reaction? 2Cr2O7 B)  FeCl3 C)  I2 D)  Ag2O" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   H2Cr2O7
B)   FeCl3
C)   I2
D)   Ag2OE) B) and D)
F) None of the above

Question 8

Identify how you could synthesize an enamine.

Accepted Answer

A)   React a ketone or an aldehyde with a secondary amine.
B)   React a ketone or an aldehyde with a primary amine.
C)   React a ylide with a primary amine.
D)   React a ylide with a secondary amine.E) A) and B)
F) None of the above

Question 9

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

Accepted Answer

A)   I only
B)   II only
C)   III only
D)   II and IIIE) A) and B)
F) C) and D)

Question 10

Which of the following products is (are)  formed by Wittig reaction of CH3CH2CH2CHO with Ph3P = CHCH3? 3CH2CH2CHO with Ph3P = CHCH3?   A)  Only I B)  Only II C)  Only III D)  Only I and II" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

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

Question 11

What is the missing reagent in the reaction below?

Accepted Answer

A)   Methanol, acid
B)   Ethanol, acid
C)   NaOEt
D)   NaOMeE) A) and C)
F) A) and D)

Question 12

Using IR spectroscopy, how can you tell the difference between a ketone and an aldehyde?

Accepted Answer

A)   A ketone has no carbonyl stretch at 1720 cm-1.
B)   An aldehyde has a carbonyl stretch at 1820 cm-1.
C)   An aldehyde has two C-H stretches between 2700-2850 cm-1.
D)   A ketone has no C-H stretches.E) C) and D)
F) A) and B)

Question 13

What is the structure of 2-trifluoromethyl-2-methoxybutanal?

Accepted Answer

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

Question 14

What compound is consistent with the following 1H NMR spectrum? 1H NMR spectrum?   A)  Acetone B)  Propanal C)  Cyclobutanone D)  2-butanone" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)   Acetone
B)   Propanal
C)   Cyclobutanone
D)   2-butanoneE) C) and D)
F) All of the above

Question 15

What would you use to prepare the following ylide from the starting phosphonium salt?

Accepted Answer

A)   butyl lithium
B)   1-bromo-2-methylpropane
C)   triphenylphosphine
D)   acetic acidE) A) and B)
F) All of the above

Question 16

What is the missing reagent in the reaction below?

Accepted Answer

A)   Ethyl amine, mild acid
B)   Diethylamine, mild acid
C)   Diethylamine, strong acid
D)   Diethylamine, NaOMeE) A) and D)
F) None of the above

Question 17

What is the first step in nucleophilic addition under acidic conditions?

Accepted Answer

A)   Protonation of the nucleophile
B)   Addition of the nucleophile
C)   Loss of water
D)   Protonation of the carbonylE) None of the above
F) A) and B)

Question 18

What is the product?

Accepted Answer

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

Question 19

What is the product of the following sequence of reactions?

Accepted Answer

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

Question 20

Which of the following will have the highest wave number for the carbonyl stretch in the IR spectrum?

Accepted Answer

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

Exam 21: Aldehydes and Ketones Nucleophilic Addition

What is the product of the following sequence of reactions?

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What compound is consistent with the following 1H NMR spectrum?

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What is the structure of 3-methylcyclohexanone?

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What sequence of reactions is required for the following transformation?

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Which of the following products is (are) formed by Wittig reaction of CH3CH2CH2CHO with Ph3P = CHCH3?

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Which of the following will have the highest wave number for the carbonyl stretch in the IR spectrum?

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What is the product?

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Why can't you use acidic conditions (such as aqueous hydrochloric acid) for the addition of a Grignard reagent to a ketone?

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Identify how you could synthesize an enamine.

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

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What is the missing reagent in the reaction below?

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What is the major organic product obtained from the following sequence of reactions?

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What is the first step in nucleophilic addition under acidic conditions?

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Name the following aldehyde.

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What is the missing reagent in the reaction below?

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Which of the following oxidants would work for the following reaction?

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What is the product of the following reaction?

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What would you use to prepare the following ylide from the starting phosphonium salt?

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What is the structure of 2-trifluoromethyl-2-methoxybutanal?

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Using IR spectroscopy, how can you tell the difference between a ketone and an aldehyde?

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What compound is consistent with the following ¹H NMR spectrum?

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Which of the following products is (are) formed by Wittig reaction of CH₃CH₂CH₂CHO with Ph₃P = CHCH₃?

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