Question

Please help provide stepwise mechanisms for each product with arrows

1. (5.75pts) Provide a stepwise mechanism showing how each of the products below are formed OH H,SO

Answer 1

This reaction is an example of hydration reaction of alkene via a carbocation rearrangement as shown below. H2SO4 + H2O H30+ In the first step, water on reaction with sulfuric acid give hydronium ion intermediate. OH HH -H2O Alkene on electrophilic addition reaction with hydronium ion give a carbocation intermediate which on addition of water followed by proton transfer give the product as shown here. он de o methyl shift -H2O -H* For the other products formation, generation of carbocation at the other end of the alkene followed by methyl shift to give stable tertiary carbocation intermediate then addition of water and proton removal give product Il as shown here. methylene shift CH methylene group shift then addition of water and proton removal give five membered ring product Ill as shown here.