kayleighnewnum7928 kayleighnewnum7928
  • 23-01-2020
  • Chemistry
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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?

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pstnonsonjoku
pstnonsonjoku pstnonsonjoku
  • 23-01-2020

Answer: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.

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