Question 1

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 A

Question 2

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 A

Question 3

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. A

Question 4

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 5

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 6

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 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 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

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 10

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 11

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 12

What is the IUPAC name for the following compound?

Accepted Answer

A)  pivaldehyde 
B)  2,2-dimethylpropanal 
C)  tert-butyl aldehyde 
D)  2,2-dimethylpentanal 
A)  pivaldehyde 
B)  2,2-dimethylpropanal 
C)  tert-butyl aldehyde 
D)  2,2-dimethylpentanal

Question 13

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 14

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 15

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 16

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 17

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

Question 18

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 19

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 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 21: Aldehydes and Ketones Nucleophilic Addition

What is the product of the following reaction?

Which is the most reactive carbonyl compound?

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

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

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

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

What is the product of the following reaction?

What is the product of the following reaction?

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

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

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

What is the IUPAC name for the following compound?

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 IUPAC for the following compound?

What is the product of the following reaction?

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

What is the missing reagent in the reaction below?

What is the product of the following reaction?

What is the driving force for the Wittig reaction?

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 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

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