Question 1

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 D

Question 2

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. 
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. B

Question 3

What is the missing reagent in the reaction below?

Accepted Answer

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

Question 4

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 5

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 6

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) Acetal 
A) Hemiacetal 
B) Di-ether 
C) Di-alkoxy alkane 
D) Acetal

Question 7

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 8

What is the structure of benzophenone?

Accepted Answer

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

Question 9

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 10

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. 
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.

Question 11

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. 
A) aqueous acid. 
B) aqueous base. 
C) oxidizing reagents. 
D) reducing reagents.

Question 12

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

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

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 15

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. 
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.

Question 16

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 17

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 18

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 19

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 20

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

Accepted Answer

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

Exam 21: Aldehydes and Ketones Nucleophilic Addition

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

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

What is the missing reagent in the reaction below?

What is the product of the following reaction?

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

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

What is the product of the following reaction?

What is the structure of benzophenone?

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

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

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

What sequence of reactions is required for the following transformation?

What is the product of the following reaction?

What is the product of the following reaction?

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

What is the product of the following reaction?

Identify how you could synthesize an enamine.

What is the missing reagent in the reaction below?

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

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

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;

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

Synthetic Polymers

Lipids

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?

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