The orientation is Markovnikov since the proton has added to the least highly substituted end,and the hydroxyl to the most highly substituted end. The regiochemistry is explained by the intermediate carbocation: HH HH H + -CH3 H CH3 H 2° 10 The secondary carbocation is more stable than the primary carbocation The reaction of dilute acid to hydrate alkenes is not a fantastic practical route due to insolubility problems,and typically two other indirect approaches are used. (1)Addition of sulfuric acid followed by hydrolysis (2)Oxymercuration-demercuration Addition of Sulfuric Acid followed by Hydrolysis The alkene reacts with conc.sulfuric acid to give an alkyl hydrogen sulfate,which then in turn is hydrolyzed to give the alcohol. +H2SO4 H20 H OSO3H H OH alkene alkyl hydrogen alcohol sulfate Cho8 Reacns of Alkenes (landscape) Page 10 Ch08 Reacns of Alkenes (landscape) Page 10 The orientation is Markovnikov since the proton has added to the least highly substituted end, and the hydroxyl to the most highly substituted end. The regiochemistry is explained by the intermediate carbocation: The secondary carbocation is more stable than the primary carbocation. The reaction of dilute acid to hydrate alkenes is not a fantastic practical route due to insolubility problems, and typically two other indirect approaches are used. (1) Addition of sulfuric acid followed by hydrolysis (2) Oxymercuration-demercuration Addition of Sulfuric Acid followed by Hydrolysis The alkene reacts with conc. sulfuric acid to give an alkyl hydrogen sulfate, which then in turn is hydrolyzed to give the alcohol. H OSO3H + H2SO4 H OH H2O alkene alkyl hydrogen sulfate alcohol