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Practice each question, then open the answer or worked solution.
Show how would you synthesise the following alcohols from appropriate alkenes.
The alcohols given above can be synthesized by applying Markovnikov’s rule of acid-catalyzed hydration of appropriate alkenes.
Acid-catalyzed hydration of pent-2-ene also produces pentan-2-ol but along with pentan3-
ol.
Thus, the first reaction is preferred over the second one to get pentan-2-ol.
(iv)
When 3-methylbutan-2-ol is treated with HBr, the following reaction takes place:
Give a mechanism for this reaction.
(Hint : The secondary carbocation formed in step II rearranges to a more stable tertiary carbocation by a hydride ion shift from 3rd carbon atom.
The steps of the reaction given above involve the following procedure :
Step 1 : Protonation
Step 2 : Forming 2 ° carbonation by eliminating the water molecule
Step 3 : Re – arranging by the shifting hydride – ion
Step 4 : Nucleophilic attack
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