How would you synthesize an alcohol from appropriate alkenes?

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Solution

Since addition and elimination are opposite to each other, the general strategy is to first dehydrate alcohol to give either a single alkene or a mixture of alkenes. If a mixture of alkenes is possible, find out which of the alkenes will give the desired alcohol. The acid-catalysed addition of $H_{2} O$ to alkenes occurs in accordance with Markovnikov's rule.

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Show how would you synthesise the following alcohols from appropriate alkenes?

(i)

(ii)

(iii)

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Show how will you synthesize:

(i) 1-phenylethanol from a suitable alkene.

(ii) cyclohexylmethanol using an alkyl halide by an S_N2 reaction.

(iii) pentan-1-ol using a suitable alkyl halide?

How would you distinguish experimentally between an alcohol and a carboxylic acid?

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