Deck 12: Oxidation and Reduction

Question 1

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

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

Answer 1

III > I > II

Question 2

What is the correct classification of the following reaction?

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

Answer 2

Reduction reaction

Question 3

What is the correct classification of the following reaction?

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

Answer 3

Reduction reaction

Question 4

What is the correct classification of the following reaction?

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

Question 5

What is the correct classification of the following reaction?

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

Question 6

Determine the product(s) of the following reaction.

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

Question 7

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

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

Question 8

What happens to the carbon atom in the transformation of chloromethane to methyllithium? CH₃Cl + 2Li $\to$ CH₃Li + LiCl

A) Oxidized
B) Reduced
C) Oxidized and Reduced
D) Neither oxidized nor reduced

Question 9

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?

A) Compound X has 3 rings.
B) Compound X has 3 $\pi$ bonds.
C) Compound X has 1 ring and 2 $\pi$ bonds.
D) Compound X has 2 rings and 1 $\pi$ bond.

Question 10

What is the correct classification of the following reaction?

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

Question 11

What is the correct classification of the following reaction?

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

Question 12

What is the correct classification of the following reaction?

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

Question 13

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

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 14

Determine the product of the following reaction.

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

Question 15

What is the correct classification of the following reaction?

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

Question 16

Rank the following compounds in order of decreasing oxidation level, putting the compound with the highest oxidation level first.

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

Question 17

Rank the following compounds in order of increasing oxidation level (from lowest to highest).

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

Question 18

Which of the following statements about oxidation and reduction is not true?

A) The conversion of an alkyne to an alkene is reduction.
B) The conversion of an alkene to an alkane is reduction.
C) Oxidation results in a decrease in the number of C-H bonds.
D) Reduction results in an increase in the number of C-Z bonds.

Question 19

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

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

Question 20

What is the correct classification of the following reaction?

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

Question 21

Determine the product of the following reaction.

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

Question 22

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

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

Question 23

Which of the following products do not form in the following reaction?

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

Question 24

What is the starting material in the following sequence of reactions?

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

Question 25

After ozonolysis and treatment of the unstable ozonide with CH₃SCH₃, compound A was converted to the compound below. What is the structure of compound A?

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

Question 26

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

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

Question 27

What reagent is required to accomplish the following transformation?

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

Question 28

What is the starting material in the following reaction?

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

Question 29

Determine the product of the following reaction.

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

Question 30

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

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

Question 31

What is the reagent required to accomplish the following transformation?

A) LiAlH₄
B) [1] OsO₄; [2] NaHSO₃, H₂O
C) RCO₃H, H₂O/HO^-
D) PCC/CH₂Cl₂

Question 32

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

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

Question 33

Determine the product of the following reaction.

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

Question 34

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

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

Question 35

What reagent is required to accomplish the following transformation?

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

Question 36

Determine the product of the following reaction, ignoring stereochemistry.

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

Question 37

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

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

Question 38

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

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

Question 39

What is the reagent required to accomplish the following transformation?

A) [1] OsO₄; [2] NaHSO₃, H₂O
B) KMnO₄, H₂O/HO^-
C) RCO₃H/H₂O/HO^-
D) PCC/CH₂Cl₂

Question 40

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

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 S_N1 mechanism.
D) The nucleophile, H^-, is a weak nucleophile.

Question 41

Determine the product of the following reaction.

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

Question 42

What is the product of the following reaction?

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

Question 43

Predict the major product of the following reaction.

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