question_answer

  (i) Di-tertbutyl ether cannot be made by Williamson's Synthesis. Explain why?                                                    2 (ii) Why the dipole moments of phenols smaller than alcohols.     (Value Based)                                                                 1

Answer:

                  (i) To prepare di tert-butyl ether by Williamson's synthesis, we need tert-butyl bromide ans Sodium                 tertiarybutoxide. Since tert-butyl bromde being 3°- alkyl halide prefers toundergo elimination rather than                 substitution, therefore the product obtained is isobulylene rather than ditertiary butyl ether.                    3                                                         (ii) Due to electron-withdrawing effect of the benzene ring, the bond in phenol is less polar but in case of methanol due to electron-donating effect of  group, bond is more polar.