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Which of the following reacitons would g...

Which of the following reacitons would give the best yield of `t-`butyl methyl ether?

A

`(CH_(3))_(3)C-Br+CH_(3)ONa rarr`

B

`(CH_(3))_(3)C-OH overset(H_(2)SO_(4))underset(140^(@)C)rarr`

C

`(CH_(3))_(3)C-OK+CH_(3)Br rarr`

D

`(CH_(3))_(3)C-Br+CH_(3)OH rarr`

Text Solution

Verified by Experts

The correct Answer is:
C
It consists of an `S_(n)^(2)` reaciton of alkoxide with bromide.

Reaction `(1)` and `(2)` lead to the formation of alkene, `(CH_(3))_(2)C=CH_(2)` through elimination. In reaction `(4)`, an alcohol rather than an alkoxide can be used in the Williamson synthesis provided we add `Ag_(2)O` which catalyzes the removal of the halide ion as `AgX`. The `OH` group of `ROH` is then a strong enough nucleophile to effect the displacement.
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