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Which of the following alkyl halides undergoes the fastest SN2 reaction with sodium cyanide, NaCN?


A) methyl iodide
B) ethyl iodide
C) 2-iodopropane
D) tert-butyl iodide

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

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Classify each of the following species ,Place the letter of the choice in the blank to the left of the formula. -________ Classify each of the following species ,Place the letter of the choice in the blank to the left of the formula. -________   A) an electrophile. B) a nucleophile. C) either an electrophile or a nucleophile.


A) an electrophile.
B) a nucleophile.
C) either an electrophile or a nucleophile.

D) B) and C)
E) All of the above

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Which of the following solvents is the best choice for the reaction of 1-chlorohexane with sodium bromide?


A) dimethylsulfoxide
B) water
C) hexane
D) toluene, PhCH3

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

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Which of the following anions is the most nucleophilic in polar protic solvents?


A) F-
B) Cl-
C) Br-
D) I-

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

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Which of the following statements is not true regarding SN1 reactions?


A) A carbocation intermediate is formed.
B) The mechanism has only one step.
C) Polar, protic solvents are good choices for SN1 reactions.
D) The stereochemical outcome is racemization at the carbon bearing the leaving group.

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

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Draw all of the chloroalkanes that undergo base-promoted dehydrochlorination to form the following alkene? Draw all of the chloroalkanes that undergo base-promoted dehydrochlorination to form the following alkene?

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The following reaction would have a faster rate in a higher polarity solvent than one of low polarity. The following reaction would have a faster rate in a higher polarity solvent than one of low polarity.

A) True
B) False

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Which of the following anions is the most nucleophilic in polar aprotic solvents?


A) F-
B) Cl-
C) Br-
D) I-

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

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What is the major organic product obtained from the following reaction? What is the major organic product obtained from the following reaction?

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What is the major organic product obtained from the following reaction? What is the major organic product obtained from the following reaction?   A) 1 B) 2 C) 3 D) 4


A) 1
B) 2
C) 3
D) 4

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

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Which of the following energy diagrams represents the course of an exothermic SN2 reaction? Which of the following energy diagrams represents the course of an exothermic S<sub>N</sub>2 reaction?   A) 1 B) 2 C) 3 D) 4


A) 1
B) 2
C) 3
D) 4

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

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