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NEETChemistryGeneral Organic Chemistry

The heterolytic cleavage of the C - Br bond in 2-bromo-2-methylbutane yields a carbocation intermediate. What is the number of hyperconjugative structures possible for this resulting carbocation?

Options

  1. A9
  2. B6
  3. C5
  4. D8

Correct answer

D. 8

Step-by-step solution

First, deduce the structure of the starting compound. 2-Bromo-2-methylbutane is CH ₃- C ( Br )( CH ₃)- CH ₂- CH ₃ . Heterolytic cleavage of the C - Br bond results in the formation of the 2-methylbutan-2-yl carbocation: CH ₃- C ^+( CH ₃)- CH ₂- CH ₃ . To find the number of hyperconjugative structures, count the number of -hydrogens attached to the carbons directly bonded to the positively charged carbon. The -carbons are: - C1 methyl group: 3 -hydrogens - C2 methyl branch: 3 -hydrogens - C3 methylene group: 2 -hydr

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