JEE Main levelSingle correct optionDifficulty 2 of 3ap207
The best Williamson route to tert-butyl methyl ether, (CHX3)X3C−O−CHX3, is
A(CHX3)X3C−ONa with CHX3I
BCHX3ONa with (CHX3)X3C−Br
C(CHX3)X3C−OH with CHX3OH and NaOH
DCHX3ONa with (CHX3)X3C−OH
Answer: A
The alkyl halide must be primary (or methyl) so that SN2 wins over E2. Sodium tert-butoxide with CHX3I gives the ether, while CHX3ONa with tert-butyl bromide gives 2-methylpropene by elimination.