Question 1

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 2

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 3

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 4

Which of the following statements about carbohydrates is not true?

Accepted Answer

A) Carbohydrates are sugars and starches. 
B) Carbohydrates often contain acetals and hemiacetals. 
C) In solution, glucose is in the cyclic acetal form only. 
D) Glucose can form a cyclic hemiacetal from the acyclic polyhydroxy aldehyde. 
A) Carbohydrates are sugars and starches. 
B) Carbohydrates often contain acetals and hemiacetals. 
C) In solution, glucose is in the cyclic acetal form only. 
D) Glucose can form a cyclic hemiacetal from the acyclic polyhydroxy aldehyde.

Question 5

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 6

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 7

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 8

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

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

Is the following reaction reversible and, if so, under what conditions?

Accepted Answer

A) No 
B) Yes, under acidic conditions 
C) Yes, using Pd/C 
D) Yes, under basic conditions 
A) No 
B) Yes, under acidic conditions 
C) Yes, using Pd/C 
D) Yes, under basic conditions

Question 12

What is the IUPAC for the following compound?

Accepted Answer

A) 1-Formyl-2-nitropropane 
B) 1-Formyl-3-nitrobutane 
C) 2-Nitrobutanal 
D) 3-Nitrobutanal 
A) 1-Formyl-2-nitropropane 
B) 1-Formyl-3-nitrobutane 
C) 2-Nitrobutanal 
D) 3-Nitrobutanal

Question 13

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 14

Butanal (MW= 72) has a boiling point of 76 °C while butanol (MW= 74) has a boiling point of 118 °C.What accounts for this difference in boiling points?

Accepted Answer

A) Butanol is polar while butanal is not polar. 
B) Butanol can exhibit dipole-dipole interactions while butanal cannot. 
C) Butanol can hydrogen bond and butanal cannot hydrogen bond. 
D) Butanal is less sterically hindered than butanol. 
A) Butanol is polar while butanal is not polar. 
B) Butanol can exhibit dipole-dipole interactions while butanal cannot. 
C) Butanol can hydrogen bond and butanal cannot hydrogen bond. 
D) Butanal is less sterically hindered than butanol.

Question 15

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 16

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 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

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 19

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 20

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

Exam 21: Aldehydes and Ketones Nucleophilic Addition

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

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

Which is the most reactive carbonyl compound?

Which of the following statements about carbohydrates is not true?

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

What is the product of the following reaction?

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

What is the product of the following reaction?

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

What is the product of the following reaction?

Is the following reaction reversible and, if so, under what conditions?

What is the IUPAC for the following compound?

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

Butanal (MW= 72) has a boiling point of 76 °C while butanol (MW= 74) has a boiling point of 118 °C.What accounts for this difference in boiling points?

What is the driving force for the Wittig reaction?

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

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

What is the missing reagent in the reaction below?

What is the product of the following sequence of reactions?

What is the structure of 3-methylcyclohexanone?

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

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