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From what I leart from my teacher is that 4-(tribromomethyl) benzoic acid is more acidic than 4-(trichloromethyl) benzoic acid. But I'm not sure what the reason is.According to me 4-(trichloromethyl) benzoic acid should be more acidic since Cl will exert much stronger -I effect and also hyper conjugation effect than Br.

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