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Explain why following reaction give different products : |
Answer» Solution :When reacting with weak nucleophiles under acidic conditions, epoxides react via an `S_(N)2` type mechanism. Attack occurs at the least hindered carbon atom. When reacting with weak nucleophiles under acidic conditions, epoxides react via an `S_(N)1` type mechanism. Since the nucleophile is weak, it attacks the carbon with the largest amount of `DELTA+` CHARGE, regardless of steric hindrance. This large amount of charge RESIDES where it is most stable, in this case, on the more substituted carbon. Additional charge stabilization results from resonance with the benzene ring. 
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