2-chloro-2-methylpentane on reaction with sodium methoxide in methanol yields (A) `C_2H_5CH_2overset(CH_3)overset(|)underset(CH_3)underset(|)C-OCH_3`
(B) `C_2H_5 CH_2underset(CH_3)underset(|)C=CH_2`
(C ) `C_2H_5 CH=underset(CH_3)underset(|)C-CH_3`

Options

A. (iii) only
B. (i) and (ii)
C. All of these
D. (i) and (iii)

Answer

A

Explanation

When lert -alkyl halides are used in Williamson synthesis elimination occurs rather than substitution resulting into formation of alkene. Here alkoxide ion abstract one of the B-hydrogen atom along with acting as a nucleophile.
`CH_3-CH_2-CH_2-overset(CH_3)overset(|)underset("2-Chloro-2-methylpentane")underset(Cl)underset(|)(C)-CH_3+Na^(-)OCH_3overset(CH_3OH)rarrunderset("2-Metehyl pent-2-ene")(CH_3CH_2)-overset(H)overset(|)C=overset(CH_3)overset(|)C-CH_3+CH_3OH+NaBr`