(Solved): IV. The acid-catalyzed electrophilic addition of ethanol to 1-methylstyrene (shown below) produces ...

IV. The acid-catalyzed electrophilic addition of ethanol to 1-methylstyrene (shown below) produces two possible regioisomeric ethers in unequal amounts. (30 pts total) ol H?SO4 (dil) Ph A. Provide an electron-pushing mechanism for the reaction of sulfuric acid with ethanol. Include an appropriate reaction arrow and an approximate pK, value for all acids present. (3 pts) B. For the electrophilic addition of ethanol to 1-methylstyrene (shown above), provide an electron- pushing mechanism that accounts for the major and minor product. Use acids and bases in this reaction mechanism that are consistent with the acid/base reaction in part A Be sure to show all appropriate arrows, lone pairs, formal charges, intermediates, stereochemistry, bonds, resonance, etc... (9 pts) C. This reaction cannot proceed under the conditions shown below. Explain why no reaction is possible. under these conditions. (3 pts) O-H No reaction 5