Question:
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.
Solution:
The mechanism of the given reaction involves the following steps:
Step 1: Protonation
Step 2: Formation of 2° carbocation by the elimination of a water molecule
Step 3: Re-arrangement by the hydride-ion shift
Step 4: Nucleophilic attack
