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Exam 7: Haloalkanes

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Question 31

Multiple Choice

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Which reactions proceed according to an E2 mechanism?

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

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

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Question 32

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Polar aprotic solvents favor S_N1 reactions.

A) True
B) False

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Question 33

Multiple Choice

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Which of the reactions below are most likely to be S_N2 reactions?

What product is formed in the E1 reaction shown below?

Which reaction below proceeds via an E2 mechanism?

Which reaction proceeds according to an E1 mechanism?

1-chloro-4-(chloromethyl)cyclohexane reacts if heated until HCl leaves the molecule. What is the chemical structure of the product?

Which statements apply to an S_N2 reaction? I. The rate limiting step of the reaction involves the alkyl halide and the nucleophile. II. The order of reactivity is methyl > 1°>2°>3°. III. The rate limiting step of the reaction involves only the alkyl halide. IV. There is an intermediate carbocation.

What is the major product from an elimination reaction starting with 2-bromopentane?

Which reactions will proceed with inversion of configuration?

Which solvents are polar protic? I. ethanol II. hexane III. DMSO IV. water

Which of the reactions below are most likely to be S_N1 reactions?

Which is the best reaction condition for preparing 2-iodohexane from 1-hexene?

Which statements apply to an S_N1 reaction? I. The rate limiting step of the reaction involves the alkyl halide and the nucleophile. II. The order of reactivity is methyl < 1°< 2° < 3°. III. The rate limiting step of the reaction involves only the alkyl halide. IV. There is an intermediate carbocation.

1-Chloro-4-(chloromethyl)cyclohexane reacts with two molecules of potassium-tert-butoxide in dimethylformamide. What are the two intermediate reaction products and the final reaction product formed?

The major product of the reaction of R-2-bromobutane with water is a racemic alcohol.

The major product of the reaction of bromocyclohexane and potassium tert-butoxide in water is an ether.

1-bromo-4-(bromomethyl)cyclohexane reacts with potassium methylthiolate in dimethylsulfoxide. Draw the chemical structure of the product that is formed at room temperature?