Alkyl Halides and Aryl HalidesHard

Question

In which of the following reaction the product obtained is t-butyl methyl ether ?

Options

A.CH3OH + HO - CH2 - CH3
B.
C.CH3Br + Na+O- -
D.CH3 - O-Na+ + CH3 -

Solution

It is Williamson′s synthesis. It involves the nucleophilic attack of alkoxide ion on alkyl halide according to SN2 mechanism. In order to methyl halide (primary) and sodium tertiary butoxide, but not sodium ethoxide and t-alkyl halide because the latter undergoes elimination reaction rather than substitution

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