Hoping to synthesize 3,3-dimethyl-2-butanol, an inexperienced student reacted 3,3-dimethyl-1-butene with h2so4 / h2o. what major product was the student surprised to isolate?

2,3-dimethyl-2-butanol

Explanation:

From the mechanism shown below, the addition of H^+ produces secondary carbocation which is less stable and rearranges by 1,2-alkyl shift to form a more stable tertiary carbocation which onto which the HSO3- now adds. Reaction with water gives the 2,3-dimethyl-2-butanol as the major product. The minor product is 3,3-dimethyl butanol. The alkyl shift is to relieve steric hindrance and create a more stable carbocation.