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Carbocations: Factors affecting their Stability

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A carbocation is a species where a carbon atom bonds to three carbon atoms and has a positive charge. Carbocations are electron deficient species and therefore very reactive and unstable . Anything which donates electron density to the electron-deficient center will help to stabilize them. Factors that stabilize them are the following:  Neighboring carbon atoms (inductive effect) Neighboring carbon-carbon multiple bonds (resonance effect) Neighboring atoms with lone pairs (resonance effect) How carbocations are stabilized by neighboring carbons atoms? The stability of carbocations decreases as the number of carbons attached to the C+ decreases. That means that tertiary carbocations are more stable than secondary that in turn are more stable than primary (Fig. 1). Fig. 1: Carbocation stability increases as methyl substitution increases around the electron deficient carbon C+. The methyl groups (-CH 3 ) are electron donating and therefore stabilize the positive charge (inductive ...