Question 1

Rank the following alkenes in order of decreasing heat of hydrogenation.

Accepted Answer

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

Question 2

What reagent is required to accomplish the following transformation?

Accepted Answer

A)  Na, NH3 
B)  H2, Pd-C 
C)  H2, Ni 
D)  H2, Lindlar catalyst 
A)  Na, NH3 
B)  H2, Pd-C 
C)  H2, Ni 
D)  H2, Lindlar catalyst

Question 3

Which of the following statements about the reduction of epoxides with LiAlH4 is true?

Accepted Answer

A)  The nucleophile is a hydride (H-). 
B)  In unsymmetrical epoxides, nucleophilic attack of H- occurs at the more substituted carbon atom. 
C)  The reaction follows SN1 mechanism. 
D)  The nucleophile, H-, is a weak nucleophile. 
A)  The nucleophile is a hydride (H-). 
B)  In unsymmetrical epoxides, nucleophilic attack of H- occurs at the more substituted carbon atom. 
C)  The reaction follows SN1 mechanism. 
D)  The nucleophile, H-, is a weak nucleophile.

Question 4

Determine 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

Determine the product of the following reaction, ignoring stereochemistry.

Accepted Answer

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

Question 6

Which of the following explains why heats of hydrogenation cannot be used to determine the relative stability of compounds A and B below?

Accepted Answer

A)  Compound A is trisubstituted while compound B is monosubstituted. 
B)  Compound A has E configuration while compound B has no E/Z configuration. 
C)  Both compounds A and B have no E/Z configurations. 
D)  Hydrogenation of A and B give different alkanes. 
A)  Compound A is trisubstituted while compound B is monosubstituted. 
B)  Compound A has E configuration while compound B has no E/Z configuration. 
C)  Both compounds A and B have no E/Z configurations. 
D)  Hydrogenation of A and B give different alkanes.

Question 7

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

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 8

What is the correct classification of the following reaction?

Accepted Answer

A)  Reduction reaction 
B)  Oxidation reaction 
C)  Elimination reaction 
D)  Substitution reaction 
A)  Reduction reaction 
B)  Oxidation reaction 
C)  Elimination reaction 
D)  Substitution reaction

Question 9

Which of the following is (are) formed by ozonolysis of compound A?

Accepted Answer

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

Question 10

Which of the following classes of organic compounds cannot undergo reduction easily?

Accepted Answer

A)  Alkanes 
B)  Alkenes 
C)  Alkynes 
D)  Carboxylic acids 
A)  Alkanes 
B)  Alkenes 
C)  Alkynes 
D)  Carboxylic acids

Question 11

What is the correct classification of the following reaction?

Accepted Answer

A)  Reduction reaction 
B)  Oxidation reaction 
C)  Elimination reaction 
D)  Substitution reaction 
A)  Reduction reaction 
B)  Oxidation reaction 
C)  Elimination reaction 
D)  Substitution reaction

Question 12

Predict the major product of the following reaction.

Accepted Answer

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

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

Determine 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

A compound X of molecular formula C8H12 with no triple bonds reacts with one equivalent of H2 to give a new compound having molecular formula C8H14. What can be inferred about the structure of compound X?

Accepted Answer

A)  Compound X has 3 rings. 
B)  Compound X has 3 F1F1F1S1F1F1F10 bonds. 
C)  Compound X has 1 ring and 2 F1F1F1S1F1F1F10 bonds. 
D)  Compound X has 2 rings and 1 F1F1F1S1F1F1F10 bond. 
A)  Compound X has 3 rings. 
B)  Compound X has 3 F1F1F1S1F1F1F10 bonds. 
C)  Compound X has 1 ring and 2 F1F1F1S1F1F1F10 bonds. 
D)  Compound X has 2 rings and 1 F1F1F1S1F1F1F10 bond.

Question 16

What is the correct classification of the following reaction?

Accepted Answer

A)  Reduction reaction 
B)  Oxidation reaction 
C)  Elimination reaction 
D)  Substitution reaction 
A)  Reduction reaction 
B)  Oxidation reaction 
C)  Elimination reaction 
D)  Substitution reaction

Question 17

What is the correct classification of the following reaction?

Accepted Answer

A)  Reduction reaction 
B)  Oxidation reaction 
C)  Elimination reaction 
D)  Substitution reaction 
A)  Reduction reaction 
B)  Oxidation reaction 
C)  Elimination reaction 
D)  Substitution reaction

Question 18

What is the correct classification of the following reaction?

Accepted Answer

A)  Reduction reaction 
B)  Oxidation reaction 
C)  Elimination reaction 
D)  Substitution reaction 
A)  Reduction reaction 
B)  Oxidation reaction 
C)  Elimination reaction 
D)  Substitution reaction

Question 19

What is the correct classification of the following reaction?

Accepted Answer

A)  Reduction reaction 
B)  Oxidation reaction 
C)  Elimination reaction 
D)  Substitution reaction 
A)  Reduction reaction 
B)  Oxidation reaction 
C)  Elimination reaction 
D)  Substitution reaction

Question 20

Rank the following alkenes in order of increasing rate of hydrogenation.

Accepted Answer

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

Exam 12: Oxidation and Reduction

Rank the following alkenes in order of decreasing heat of hydrogenation.

What reagent is required to accomplish the following transformation?

Which of the following statements about the reduction of epoxides with LiAlH4 is true?

Determine the product of the following reaction.

Determine the product of the following reaction, ignoring stereochemistry.

Which of the following explains why heats of hydrogenation cannot be used to determine the relative stability of compounds A and B below?

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

What is the correct classification of the following reaction?

Which of the following is (are) formed by ozonolysis of compound A?

Which of the following classes of organic compounds cannot undergo reduction easily?

What is the correct classification of the following reaction?

Predict the major product of the following reaction.

What is the product of the following reaction?

Determine the product of the following reaction.

A compound X of molecular formula C8H12 with no triple bonds reacts with one equivalent of H2 to give a new compound having molecular formula C8H14. What can be inferred about the structure of compound X?

What is the correct classification of the following reaction?

What is the correct classification of the following reaction?

What is the correct classification of the following reaction?

What is the correct classification of the following reaction?

Rank the following alkenes in order of increasing rate of hydrogenation.

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

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

Aldehydes and Ketones Nucleophilic Addition

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 statements about the reduction of epoxides with LiAlH₄ is true?

A compound X of molecular formula C₈H₁₂ with no triple bonds reacts with one equivalent of H₂ to give a new compound having molecular formula C₈H₁₄. What can be inferred about the structure of compound X?