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Question 45 of 66

Q.Which order of arrangement is correct in terms of the strength of the acid ?

(a) CH3−CH2COOH<CH3COOH<HCOOH<ClCH2COOHCH_3-CH_2COOH < CH_3COOH < HCOOH < ClCH_2COOH
(b) CH3−CH2COOH>CH3COOH<HCOOH<ClCH2COOHCH_3-CH_2COOH > CH_3COOH < HCOOH < ClCH_2COOH
(c) HCOOH>CH3CH2COOH<CH3COOH>ClCH2COOHHCOOH > CH_3CH_2COOH < CH_3COOH > ClCH_2COOH
(d) ClCH2COOH<HCOOH<CH3COOH<CH3CH2COOHClCH_2COOH < HCOOH < CH_3COOH < CH_3CH_2COOH
Tamil Nadu DgeTamil Nadu HSC (DGE) Board 2018MCQ· 1mImportance★★★★★
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Carboxylic acid strength is governed by how well the conjugate base's negative charge is stabilised: electron-donating alkyl groups (+I effect) destabilise the carboxylate and WEAKEN the acid, while electron-withdrawing groups (like −Cl-Cl, -I effect) stabilise the carboxylate and STRENGTHEN the acid.

Propanoic acid (CH3CH2COOHCH_3CH_2COOH, pKa≈4.87pK_a\approx4.87) has the longest alkyl chain (strongest +I donation) and is the weakest of the four. Acetic acid (CH3COOHCH_3COOH, pKa≈4.76pK_a\approx4.76) has a shorter alkyl group, so is slightly stronger. Formic acid (HCOOHHCOOH, pKa≈3.75pK_a\approx3.75) has NO alkyl group at all (just H), removing the destabilising +I effect entirely, making it noticeably stronger than acetic acid. Chloroacetic acid (ClCH2COOHClCH_2COOH, pKa≈2.86pK_a\approx2.86) has a strongly electron-withdrawing −Cl-Cl directly stabilising the carboxylate by i …

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