Carbocation Stability in Prop-1-enylbenzene

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The discussion centers on the stability of carbocations in prop-1-enylbenzene, specifically comparing the stability when the positive charge is on the carbon directly attached to the benzene ring versus the second carbon. The carbocation is more stable when the positive charge is on the carbon adjacent to the benzene due to the resonance stabilization provided by the benzyl group, which effectively neutralizes the positive charge through inductive effects. In contrast, a secondary carbon is less stable because the phenyl group, while an electron-withdrawing group that destabilizes carbocations through inductive effects, can still stabilize them via resonance. Participants suggest drawing resonance structures to visualize the differences in stability between the two carbocation positions.
Suraj M
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Consider:
prop-1-enylbenzene
Why is the carbocation more stable when the +ve charge is on the carbon directly attached to the benzene ring as apposed to the +ve charge on the the 2nd carbon counted from the benzene ring?
 
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Suraj M said:
Consider:
prop-1-enylbenzene
Why is the carbocation more stable when the +ve charge is on the carbon directly attached to the benzene ring as apposed to the +ve charge on the the 2nd carbon counted from the benzene ring?
Because of benzyl group which is resonance stabilized it neutralizes more the +ve charge by inductive effect as compared to a 2° carbon.
 
Raghav Gupta said:
Because of benzyl group which is resonance stabilized it neutralizes more the +ve charge by inductive effect as compared to a 2° carbon.
Phenyl group destabilises carbocations by inductive effect since it's an electron withdrawing group, but it can stabilise carbocations by resonance effect.
Try drawing the resonance structures of the compound with carbocations on the 2nd carbon.
 
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AdityaDev said:
Try drawing the resonance structures of the compound with carbocations on the 2nd carbon.
+R right? Got the structure!
 
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