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Predict the major product(s) of the following reaction. Predict the major product(s) of the following reaction. A) I B) II and IV C) III and V D) I and IV E) V


A) I
B) II and IV
C) III and V
D) I and IV
E) V

F) None of the above
G) A) and E)

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D

Which of the following processes is responsible for the fact that free radical bromination of methane is slower than free radical chlorination?


A) initiation
B) hydrogen abstraction
C) halogen abstraction
D) termination
E) entropy

F) B) and E)
G) A) and D)

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How many constitutional isomers are possible if propane is dichlorinated? Draw them.

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Which of the following shows the initiation step of monochlorination of methane? Which of the following shows the initiation step of monochlorination of methane? A) I B) II C) III D) IV E) I and II


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

F) C) and D)
G) None of the above

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A

Which of the following are major products of the reaction shown? Which of the following are major products of the reaction shown? A) I B) I, II C) I, IV D) I, III E) I, II, III, IV


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

F) C) and D)
G) B) and E)

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E

Which of the following represents a propagation step in the monochlorination of methylene chloride (CH2Cl2) ?


A) Which of the following represents a propagation step in the monochlorination of methylene chloride (CH<sub>2</sub>Cl<sub>2</sub>) ? A) B) Cl<sub>2</sub> C) D)

B) Cl2

C) Which of the following represents a propagation step in the monochlorination of methylene chloride (CH<sub>2</sub>Cl<sub>2</sub>) ? A) B) Cl<sub>2</sub> C) D)

D) Which of the following represents a propagation step in the monochlorination of methylene chloride (CH<sub>2</sub>Cl<sub>2</sub>) ? A) B) Cl<sub>2</sub> C) D)

E) A) and B)
F) All of the above

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Which of the following is expected to function as an antioxidant? Which of the following is expected to function as an antioxidant? A) I B) II C) III D) IV E) I, II, III, and IV


A) I
B) II
C) III
D) IV
E) I, II, III, and IV

F) All of the above
G) A) and E)

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Which term most accurately describes the process shown below? Which term most accurately describes the process shown below? A) hydrogen abstraction B) halogen abstraction C) homolytic cleavage D) coupling E) elimination


A) hydrogen abstraction
B) halogen abstraction
C) homolytic cleavage
D) coupling
E) elimination

F) A) and D)
G) A) and C)

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Upon treatment with NBS and irradiation with UV light, 1-ethyl-4-methylbenzene produces exactly three monobrominated compounds (including stereoisomers). Draw the products of this reaction.

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In the molecule shown below, determine which of the highlighted C-H bonds (from a to e) is expected to have the lowest bond dissociation energy. In the molecule shown below, determine which of the highlighted C-H bonds (from a to e) is expected to have the lowest bond dissociation energy. A) C-H<sub>a</sub> B) C-H<sub>b</sub> C) C-H<sub>c</sub> D) C-H<sub>d</sub> E) C-H<sub>e</sub>


A) C-Ha
B) C-Hb
C) C-Hc
D) C-Hd
E) C-He

F) C) and D)
G) B) and C)

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Which of the following is the most stable radical?


A) Which of the following is the most stable radical? A) B) C) D) E)
B) Which of the following is the most stable radical? A) B) C) D) E)
C) Which of the following is the most stable radical? A) B) C) D) E)
D) Which of the following is the most stable radical? A) B) C) D) E)
E) Which of the following is the most stable radical? A) B) C) D) E)

F) B) and D)
G) A) and D)

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Free radical chlorination of ethane can produce higher halogenation products (dichlorinated, trichlorinated, etc…) in addition to chloroethane. How could the production of higher halogenated products be minimized?


A) Use an excess of chlorine
B) Use an excess of ethane
C) Use equimolar chlorine and ethane
D) It is not possible to minimize the production of higher halogenated products

E) A) and B)
F) None of the above

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Use correct arrow formalism to draw all of the reasonable resonance structures for the radical shown below. Use correct arrow formalism to draw all of the reasonable resonance structures for the radical shown below.

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Rank the following radicals in order of decreasing stability (most stable to least stable) . Rank the following radicals in order of decreasing stability (most stable to least stable) . A) IV > I > II > III B) III > I > II > IV C) III > II > I > IV D) III > IV > II > I E) II > III > I > IV


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

F) D) and E)
G) A) and D)

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Propylene (propene) undergoes free radical polymerization with benzoyl peroxide, but does not produce very long chains. Provide a reasonable explanation for this result.

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There are C-H bonds at allylic positions...

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Use correct arrow formalism to show the mechanism of the following radical process: Use correct arrow formalism to show the mechanism of the following radical process:

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Which of the following compounds would be expected to be least destructive to the ozone layer?


A) Which of the following compounds would be expected to be least destructive to the ozone layer? A) B) C) D)
B) Which of the following compounds would be expected to be least destructive to the ozone layer? A) B) C) D)
C) Which of the following compounds would be expected to be least destructive to the ozone layer? A) B) C) D)
D) Which of the following compounds would be expected to be least destructive to the ozone layer? A) B) C) D)

E) A) and D)
F) B) and C)

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Propose an efficient synthesis of 3,4-dimethyl-2-pentanol using 2-methyl-2-butene and ethanol as your sources of carbon.

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Which term best describes the process shown below? Which term best describes the process shown below? A) neutralization B) propagation C) termination D) initiation E) elimination


A) neutralization
B) propagation
C) termination
D) initiation
E) elimination

F) A) and B)
G) C) and D)

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Draw the major product(s) of the following reaction. Is the product optically active? Explain. Draw the major product(s) of the following reaction. Is the product optically active? Explain.

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blured image The product is not ...

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