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Chapter 6: 6-22P (page 312)
Propose an SN1 mechanism for the solvolysis of 3-bromo-2,3-dimethylpentane in ethanol.
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Give a mechanism to explain the two products formed in the following reaction.
Predict the major product of the following reaction, and give a mechanism to support your prediction.
Give the structures of the following compounds.
(a) Methylene chloride
(b) Carbon tetrachloride
(c) 3-iodo-2-methylpentane
(d) Chloroform
(e) 2-chloro-3-ethyl-2-methyhexane
(f) Isobutyl iodide
(g) Cis-1-chloro-3-(chloromethyl)cyclohexane
(h) Tert-butyl bromide
(a)Optically active 2-bromobutane undergoes racemization on treatment with a solution of KBr. Give a mechanism for this racemization.
(b)In contrast, optically active butan-2-ol does not racemize on treatment with a solution of KOH. Explain why a reaction like that in part (a) does not occur.
(c)Optically active butan-2-ol racemizes in dilute acid. Propose a mechanism for this racemization.
Question: Using cyclohexane as one of your starting materials, show how you would synthesize the following compounds.
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