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Acetate ion has charge delocalisation and in Br- charge is distributed throughout the atom ,so how should they be compared?

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  • $\begingroup$ As acetate has charge delocalisation, it should be better leaving group, I guess. Bear in mind, I have not checked my answer. $\endgroup$
    – S R Maiti
    Dec 31, 2017 at 10:56

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Br anion is much larger in size than oxygen anion present in acetate ion. Hence Br anion can hold the negative charge better than oxygen atoms of acetate. Again negative charge density in Br anion is less than that on the 2 oxygen atoms of acetate. Therefore , Br anion is a weaker base than acetate and it is very well known fact that weaker base is a better leaving group or nucleofuse.

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    $\begingroup$ "it is very well known fact" doesn't make for a very good argument ;) $\endgroup$
    – airhuff
    Jan 1, 2018 at 1:36

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