question_answer 95)

  Ethers can be prepared by Williamson synthesis in which an alkyl halide is reacted with sodium alkoxide. Di-tert-butyl ether can't be prepared by this method. Explain.

Answer:

                  'Williamson's synthesis occurs by  mechanism in which sodium alkoxide reacts with an alkyi halide. Now to prepare di-tert-butyl ether, sodium fert-butoxide must be reacted with tert-butyl bromide. Since 3° alkyi halides prefer to undergo elimination rather than substitution, therefore, sodium fert-butoxid. ?S with tert-butyl bromide and favours elimination to form isobutylene rather than substitution to form di-teri- butyl ether                                                                                  Tert-Butyl bromide + Sod. Tert-butoxide