The books say chlorobenzene resists nucleophilic substitution because the C-Cl bond gets extra strength from resonance, and the incoming nucleophile faces steric hindrance from the ring. But I’ll tell you, nothing is truly unreactive if the conditions are harsh enough—just like this old Splendor, which won't start in the cold until you give it a proper, persistent kick. They taught us in class that at high temperature and pressure, with a very strong base, even chlorobenzene can be made to react. Reminds me of the stubborn bolt on my carrier rack that finally gave way after I soaked it in oil for a week and used my full weight; sometimes, yaar, you just need the right persuasion.
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