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Explain why treatment of propyl alcohol with bromide ion fails to give propyl bromide, but treatment...

Explain why treatment of propyl alcohol with bromide ion fails to give propyl bromide, but treatment with HBr succeeds. Show a reasonable reaction mechanism using the curved arrow formalism in each and every step to support your answer.

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I - CH₃ CH₂ - e-OH e - NO I substitution reaction. propyl alcohol -OH is not a good leaving group as e-o bond is so strong

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