Question 1

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, NaOMe 
A)  Ethyl amine, mild acid 
B)  Diethylamine, mild acid 
C)  Diethylamine, strong acid 
D)  Diethylamine, NaOMe

Question 2

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

Accepted Answer

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

Question 3

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

Accepted Answer

A)  Acetone 
B)  Propanal 
C)  Cyclobutanone 
D)  2-butanone 
A)  Acetone 
B)  Propanal 
C)  Cyclobutanone 
D)  2-butanone

Question 4

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. 
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.

Question 5

What is the product of the following sequence of reactions?

Accepted Answer

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

Question 6

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

Question 7

What is the structure of 3-methylcyclohexanone?

Accepted Answer

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

Question 8

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 acid 
A)  butyl lithium 
B)  1-bromo-2-methylpropane 
C)  triphenylphosphine 
D)  acetic acid

Question 9

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. 
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.

Question 10

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 11

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

Accepted Answer

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

Question 12

Name the following aldehyde.

Accepted Answer

A)  1-methylcyclopentanal 
B)  2-methylcyclopentanal 
C)  2-methylcyclopentanecarbaldehyde 
D)  1-methylcyclopentanylcarbaldehyde 
A)  1-methylcyclopentanal 
B)  2-methylcyclopentanal 
C)  2-methylcyclopentanecarbaldehyde 
D)  1-methylcyclopentanylcarbaldehyde

Question 13

What is the missing reagent in the reaction below?

Accepted Answer

A)  Methanol, acid 
B)  Ethanol, acid 
C)  NaOEt 
D)  NaOMe 
A)  Methanol, acid 
B)  Ethanol, acid 
C)  NaOEt 
D)  NaOMe

Question 14

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

Accepted Answer

A)  H2Cr2O7 
B)  FeCl3 
C)  I2 
D)  Ag2O 
A)  H2Cr2O7 
B)  FeCl3 
C)  I2 
D)  Ag2O

Question 15

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

Accepted Answer

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

Question 16

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 carbonyl 
A)  Protonation of the nucleophile 
B)  Addition of the nucleophile 
C)  Loss of water 
D)  Protonation of the carbonyl

Question 17

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. 
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.

Question 18

What is the product?

Accepted Answer

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

Question 19

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

Accepted Answer

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

Question 20

What sequence of reactions is required for the following transformation?

Accepted Answer

A)  [1] NaOMe, [2] acetone 
B)  [1] Ph3P, [2] acetone 
C)  [1] Ph3P, [2] KOtBu, [3] acetone 
D)  acetone, heat 
A)  [1] NaOMe, [2] acetone 
B)  [1] Ph3P, [2] acetone 
C)  [1] Ph3P, [2] KOtBu, [3] acetone 
D)  acetone, heat

Exam 21: Aldehydes and Ketones Nucleophilic Addition

What is the missing reagent in the reaction below?

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

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

Identify how you could synthesize an enamine.

What is the product of the following sequence of reactions?

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

What is the structure of 3-methylcyclohexanone?

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

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

What is the product of the following reaction?

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

Name the following aldehyde.

What is the missing reagent in the reaction below?

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

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

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

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

What is the product?

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

What sequence of reactions is required for the following transformation?

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 Epoxides

Alkenes

Alkynes

Oxidation and Reduction

Mass Spectrometry and Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Radical Reactions

Conjugation, Resonance, and Dienes

Benzene and Aromatic Compounds

Electrophilic Aromatic Substitution

Carboxylic Acids and the Acidity of the O-H Bond

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Carboxylic Acids and Derivatives

Substitution Reactions of Carbonyl Compounds at the Alpha-Carbon

Carbonyl Condensation Reactions

Amines

Carbon-Carbon Bond Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Lipids

Synthetic Polymers

Filters

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

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