Question 1

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) All of the above
F) C) and D) D

Question 2

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) C) and D)
F) A) and B)

Question 3

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 D)
F) B) and C)

Question 4

Using 1H NMR spectroscopy, how can you tell the difference between an aldehyde and a ketone?

Accepted Answer

A)  An aldehyde has a C-H stretch (one or two)  between 2700-2830 cm-1.
B)  An aldehyde has a proton signal between 9-10 ppm.
C)  A ketone has signals around 2-3 ppm.
D)  A ketone has a signal around 200 ppm.E) A) and B)
F) A) and D)

Question 5

Cyclic acetals are used as protecting groups for ketones or aldehydes because they are inert to all of the following reagents except

Accepted Answer

A)  aqueous acid.
B)  aqueous base.
C)  oxidizing reagents.
D)  reducing reagents.E) None of the above
F) All of the above

Question 6

What is the missing reagent in the reaction below?

Accepted Answer

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

Question 7

What is the cyclic hemiacetal product formed from intramolecular cyclization of the following hydroxy aldehyde?

Accepted Answer

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

Question 8

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) A) and B)
F) None of the above

Question 9

What is the product of the following reaction?

Accepted Answer

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

Question 10

Why are strongly acidic conditions not used in the formation of enamines and imines?

Accepted Answer

A)  The carbonyl will be protonated.
B)  The amine will be completely protonated.
C)  The product is not stable to strong acid.
D)  An enol will be formed.E) A) and B)
F) B) and C) B

Question 11

What is the product of the following reaction?

Accepted Answer

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

Question 12

What is the product of the following reaction?

Accepted Answer

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

Question 13

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

Accepted Answer

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

Question 14

What is the product of the following reaction?

Accepted Answer

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

Question 15

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

Question 16

What is the product of the following reaction?

Accepted Answer

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

Question 17

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 C)
F) None of the above

Question 18

What is the structure of benzophenone?

Accepted Answer

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

Question 19

When an aldehyde is reacted with excess ethanol with an acid as a catalyst, what is the product called?

Accepted Answer

A)  Hemiacetal
B)  Di-ether
C)  Di-alkoxy alkane
D)  AcetalE) C) and D)
F) B) and D)

Question 20

What needs to be done to make the following reaction proceed?

Accepted Answer

A)  Heat the reaction.
B)  Add an acid catalyst only.
C)  Add a base catalyst only.
D)  Heat the reaction and add an acid catalyst.E) None of the above
F) A) and B)

Exam 21: Aldehydes and Ketones Nucleophilic Addition

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

Correct AnswerverifiedD

What is the missing reagent in the reaction below?

Correct AnswerverifiedShow Answer

Identify how you could synthesize an enamine.

Correct AnswerverifiedShow Answer

Using 1H NMR spectroscopy, how can you tell the difference between an aldehyde and a ketone?

Correct AnswerverifiedShow Answer

Cyclic acetals are used as protecting groups for ketones or aldehydes because they are inert to all of the following reagents except

Correct AnswerverifiedShow Answer

What is the missing reagent in the reaction below?

Correct AnswerverifiedC

What is the cyclic hemiacetal product formed from intramolecular cyclization of the following hydroxy aldehyde?

Correct AnswerverifiedShow Answer

What sequence of reactions is required for the following transformation?

Correct AnswerverifiedShow Answer

What is the product of the following reaction?

Correct AnswerverifiedShow Answer

Why are strongly acidic conditions not used in the formation of enamines and imines?

Correct AnswerverifiedB

What is the product of the following reaction?

Correct AnswerverifiedShow Answer

What is the product of the following reaction?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

What is the product of the following reaction?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

What is the product of the following reaction?

Correct AnswerverifiedShow Answer

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

Correct AnswerverifiedShow Answer

What is the structure of benzophenone?

Correct AnswerverifiedShow Answer

When an aldehyde is reacted with excess ethanol with an acid as a catalyst, what is the product called?

Correct AnswerverifiedShow Answer

What needs to be done to make the following reaction proceed?

Correct AnswerverifiedShow Answer

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

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D

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Using ¹H NMR spectroscopy, how can you tell the difference between an aldehyde and a ketone?

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C

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B

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

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