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NEETChemistryGeneral Organic Chemistry

Among the following substituted cyclohexyl carbocations, which one is stabilized by the maximum number of hyperconjugative structures?

Options

  1. A1-tert-Butylcyclohexyl cation
  2. B1-Ethylcyclohexyl cation
  3. C1-Methylcyclohexyl cation
  4. D1-Isopropylcyclohexyl cation

Correct answer

C. 1-Methylcyclohexyl cation

Step-by-step solution

The number of hyperconjugative structures for a carbocation is equal to the number of -hydrogens attached to the positively charged carbon. For the 1-methylcyclohexyl cation, the positively charged carbon is attached to a methyl group (which provides 3 -hydrogens) and two adjacent ring carbons (which provide 2 -hydrogens each). Total -hydrogens = 3 + 2 + 2 = 7 . For the 1-ethylcyclohexyl cation, the ethyl group provides 2 -hydrogens. Total -hydrogens = 2 + 4 = 6 . For the 1-isopropylcyclohexyl cation, the isopropyl

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