explain why cleavage of phenyl alkyl ethers with HBr always produce phenol and alkyl bromide and not bromobenzene and alkanols.
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This is because during the reaction, the attack of halide ion occurs to the protonated ether . Due to stearic hindrance of bulky phenyl group ,the attack occurs preferably to the alkyl group forming alkyl bromide.
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please refer to the attachment !
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