Acid-catalysed hydration of 3-methylbut-1-ene gives mainly:

A3-methylbutan-1-ol
B2-methylbutan-2-ol
C2-methylbutan-1-ol
D3-methylbutan-2-ol

Answer: B

Protonation gives the secondary 3-methylbutan-2-yl cation. A 1,2-hydride shift gives the tertiary 2-methylbutan-2-yl cation, which is trapped by water to give 2-methylbutan-2-ol.

Practice General Organic Chemistry III: Reaction Intermediates More on Carbocations: formation, stability, rearrangements

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