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In question 13, chapter 8 of Clayden, the answers say that replacing COOH with COOEt results in a greater electron-withdrawing effect.


On the other hand, the book also says that COOEt can act as an electron-donor.




I'm wondering, is this just a case of induction vs resonance? If this is the case, how would you draw the resonance of COOEt acting as an electron-donor? Thanks.

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