Question 1

Which is the most reactive carbonyl compound?

Accepted Answer

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

Question 2

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 3

What is the driving force for the Wittig reaction?

Accepted Answer

A) The formation of an alkene 
B) The deprotonation of a phosphonium salt 
C) The elimination of triphenylphosphine oxide 
D) The formation of a phosphonium salt 
A) The formation of an alkene 
B) The deprotonation of a phosphonium salt 
C) The elimination of triphenylphosphine oxide 
D) The formation of a phosphonium salt

Question 4

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 5

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 6

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 7

What needs to be done to make the following reaction go to starting materials?

Accepted Answer

A) Heat the reaction. 
B) Add aqueous acid. 
C) Add aqueous base. 
D) Add water. 
A) Heat the reaction. 
B) Add aqueous acid. 
C) Add aqueous base. 
D) Add water.

Question 8

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 9

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 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. 
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.

Question 11

What product is formed when the following acetal is hydrolyzed with aqueous acid?

Accepted Answer

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

Question 12

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 13

How would the following compounds be distinguishable using IR and 1H NMR spectroscopy?

Accepted Answer

A) The 1H NMR spectrum of compound I will have two singlets. 
B) The C=O absorption in the IR spectrum of compound I will be at a higher wave number than that of compound II. 
C) The 1H NMR spectrum of compound II will have one triplet at a chemical shift of about 4. 
D) The 1H NMR spectrum of compound I will have two singlets AND the C=O absorption in the IR spectrum of compound I will be at a higher wave number than that of compound II. 
A) The 1H NMR spectrum of compound I will have two singlets. 
B) The C=O absorption in the IR spectrum of compound I will be at a higher wave number than that of compound II. 
C) The 1H NMR spectrum of compound II will have one triplet at a chemical shift of about 4. 
D) The 1H NMR spectrum of compound I will have two singlets AND the C=O absorption in the IR spectrum of compound I will be at a higher wave number than that of compound II.

Question 14

Give the IUPAC name for the following compound.

Accepted Answer

A) R-3-hydroxybutanal 
B) S-3-hydroxybutanal 
C) R-2-hydroxybutan-4-al 
D) S-2-hydroxybutan-4-al 
A) R-3-hydroxybutanal 
B) S-3-hydroxybutanal 
C) R-2-hydroxybutan-4-al 
D) S-2-hydroxybutan-4-al

Question 15

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 16

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 17

What product is formed when the following compound is hydrolyzed with aqueous acid?

Accepted Answer

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

Question 18

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 19

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 20

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

Exam 18: Aldehydes and Ketones - Nucleophilic Addition

Which is the most reactive carbonyl compound?

What is the structure of 3-methylcyclohexanone?

What is the driving force for the Wittig reaction?

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 missing reagent in the reaction below?

What needs to be done to make the following reaction go to starting materials?

What sequence of reactions is required for the following transformation?

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

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

What product is formed when the following acetal is hydrolyzed with aqueous acid?

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

How would the following compounds be distinguishable using IR and 1H NMR spectroscopy?

Give the IUPAC name for the following compound.

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

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

What product is formed when the following compound is hydrolyzed with aqueous acid?

Name the following aldehyde.

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

What is the product of the following reaction?

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 and Addition Reactions

Alkynes and Synthesis

Oxidation and Reduction

Radical Reactions

Conjugation, resonance, and Dienes

Benzene and Aromatic Compounds

Reactions of Aromatic Compounds

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Carboxylic Acids and the Acidity of the O-H Bond

Carboxylic Acids and Their Derivatives - Nucleophilic Acyl Substitution

Substitution Reactions of Carbonyl Compounds at the a Carbon

Carbonyl Condensation Reactions

Amines

Carbon-Carbon Bond-Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Synthetic Polymers

Lipids

Molecular Ion Peaks and Fragmentation Patterns

Analyzing Molecular Motion and Infrared Spectroscopy

Organic Spectroscopy Concepts

Filters

How would the following compounds be distinguishable using IR and ¹H NMR spectroscopy?

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