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(Solution) - a Propose a mechanism for the reaction of benzyl alcohol

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(a) Propose a mechanism for the reaction of benzyl alcohol with acetyl chloride to give benzyl acetate.
(b) Propose a mechanism for the reaction of benzoic acid with acetyl chloride to give acetic benzoic anhydride.
(c) Propose a second mechanism for the reaction of benzoic acid with acetyl chloride to give acetic benzoic anhydride. This time, let the other oxygen of benzoic acid serve as the nucleophile to attack the carbonyl group of acetyl chloride. Because proton transfers are fast between these oxygen atoms, it is difficult to differentiate between these two mechanisms experimentally.
(d) Propose a mechanism for the reaction of aniline with acetic anhydride to give acetanilide.
(e) Propose a mechanism for the reaction of aniline with ethyl acetate to give acetanilide. What is the leaving group in your proposed mechanism? Would this be a suitable leaving group for an SN2 reaction?

 







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