When dry hydrogen halide, HX, is dissolved in an alcohol, ROH, the resulting conducts an electric current. Upon heating, an alkyl halide RX is formed. Additional sulfuric acid speeds up the formation of RX. Except for most primary alcohols , rearrangements of the same pattern as in Sec 5.22 of Organic CChemistry, Morrison and Boyd takes place. The order of reactivity of alcohols toward HX is 3o>2o>1o<CH3. i) Propose a likely mechanism for this reaction, showing how all the facts are accounted for.

ii) The alcohol, ClCH2CHOHCH3, although formally secondary reacts slowly , and at about the rate of a primary alcohol. How do you account for this?​