JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o4164
Which pairs of reagents are suitable for preparing the ether in good yield by the Williamson method (SN2 on the alkyl halide)?
ACHX3ONa and (CHX3)X3C−Br to give CHX3−O−C(CHX3)X3
B(CHX3)X3CONa and CHX3I to give CHX3−O−C(CHX3)X3
CCX2HX5ONa and CX2HX5Br to give diethyl ether
D(CHX3)X3CONa and (CHX3)X2CH−Br to give isopropyl tert-butyl ether
Answer: B, C
The Williamson synthesis needs a methyl or primary halide. Tertiary (CHX3)X3C−Br and secondary (CHX3)X2CHBr with alkoxide mainly undergo E2, giving alkenes. Methyl iodide and ethyl bromide undergo SN2.