Textbook Question
Show how you would synthesize the following:
c. cyclohexylmethanol from an alkyl halide using an SN2 reaction
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12. Alcohols, Ethers, Epoxides and Thiols
Alcohol Synthesis
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Predict the major organic product of the following reaction.
A
B
C
D
Verified step by step guidance1
Identify the reaction type: The reaction involves the addition of water across a double bond using oxymercuration-demercuration, which is a method to hydrate alkenes.
Understand the mechanism: The first step involves the formation of a mercurinium ion intermediate by the reaction of the alkene with mercuric acetate (Hg(OAc)2) in the presence of water.
Determine regioselectivity: The water molecule attacks the more substituted carbon of the mercurinium ion, following Markovnikov's rule, leading to the formation of an organomercury alcohol intermediate.
Consider stereochemistry: The addition of water is anti to the mercurinium ion, leading to the formation of a racemic mixture of enantiomers if the starting alkene is not symmetrical.
Complete the reaction: The second step involves the reduction of the organomercury intermediate with sodium borohydride (NaBH4), replacing the mercury with a hydrogen atom, resulting in the formation of the alcohol product.
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