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Q.Explain why (CH3)3C+ is more stable than CH3CH2+ and CH3+ is the least stable cation?

Haryana BsehBoard of School Education Haryana (Senior Secondary Part-I / Class 11) 2024Subjective· 2mImportance★★★★★
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A carbocation is stabilised by electron-donating alkyl groups attached to the positively charged carbon, through the +I (inductive) effect and, more importantly, hyperconjugation (donation from adjacent C–H sigma bonds into the empty p orbital). More alkyl groups/adjacent C–H bonds means more stabilisation, so 3° > 1°(ethyl) > methyl.

A carbocation has an electron-deficient carbon with an empty p orbital. Anything that pushes electron density toward that carbon stabilises it.

  • (CH₃)₃C⁺ (tert-butyl cation): three methyl groups are attached directly to the cationic carbon. Each methyl group donates electron density both through the inductive (+I) effect and through hyperconjugation — C–H sigma bonds on the adjacent methyls can align with the empty p orbital and delocalise electron density into it. With three methyl groups, there are 9 C–H bonds available for hyperconjugation. This is the most stabilised of the three.

  • CH₃CH₂⁺ (ethyl cation): only one alkyl group (a methyl) is attached to the cationic carbon, contributing +I effect and hyperconjugation from its 3 C–H bonds. Less stabilisation than the tertiary cation, but still more than a lone methyl cation.

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