When 2-bromo-3-methylbutane is treated with aqueous KOH, it follows `S_(N)-1` mechanism. The product formed is :

Options

A. 3-Methyl-2-butanol
B. 3-Methyl-1-butanol
C. 2-Methyl-2-butanol
D. 2-Methyl-1-butanol

Answer

C

Explanation

Since `S_(N)1` mechanism involves the formation of carbocation, it undergoes rearrangement to stable carbocation.
`CH_(3)-overset(CH_(3))overset("| ")underset(H)underset("| ")"C "-overset(H)overset(|)underset(Br)underset(|)C-CH_(3)overset(-Br^(-))rarrCH_(3)-overset(CH_(3))overset("| ")underset((2^(@)))underset("H ")underset("| ")"C "-overset(H)overset(|)underset(o+)C-CH_(3)overset("Hydnde")underset("Shift")rarr underset((3^(@)))(CH_(3)-underset(o+)overset(CH_(3))overset("| ")"C "-overset(H)overset(|)underset(H)underset(|)C-CH_(3))`
`CH_(3)-underset(o+)overset(CH_(3))overset("| ")"C "-overset(H)overset(|)underset(H)underset(|)C-CH_(3)overset(OH^(-))rarr underset(" 2 - Methyl -2- butanol")(CH_(3)-overset(CH_(3))overset("| ")underset(OH)underset("| ")"C "-overset(H)overset(|)underset(H)underset(|)C-CH_(3))`