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Grade: 10
        
why tertiary alkyl halide is stable than secondry alkyl halide in SN1 reaction?
 
2 years ago

Answers : (1)

Arun
23751 Points
							
Dear student
 
A tertiary alkyl halide is more reactive and therefore less stable than a secondary alkyl halide as it reacts faster in SN1 nucleophillic substitution and does not react via SN2 due to the static hinderance of the halogen atom by the three alkyl groups attached to the carbon atom with the halogen atom attached (SN1 is faster than SN2). It reacts faster in SN1 as alkyl groups are electron donating, therefore the halogen atom is more easily lost and the tertiary carbocation formed is more stable than a secondary carbocation due to the electron pushing effect of the three surrounding alkyl groups, meaning that there is more hyperconjugation and the tertiary carbocation is at a lower energy level and therefore more stable, so the overall process is more exothermic and the reaction is more thermodynamically feasible and thus more likely to occur spontaneously at room temperature (thus tertiary alkyl halides are more reactive).
 
Regards
Arun (askIITians forum expert)
2 years ago
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