GOC and Organic Chemistry BasicshardNUMERICAL

How many of the following compounds are more acidic than acetic acid ()?GOC and Organic Chemistry Basics Chemistry Question

Question

How many of the following compounds are more acidic than acetic acid ($CH_3COOH$)? $HCOOH, ClCH_2COOH, FCH_2COOH, NC-CH_2COOH, CH_3CH_2COOH, CCl_3COOH, C_6H_5COOH$

Answer: 6

💡 Solution & Explanation

Acetic acid possesses a destabilizing $+I$ methyl group. The compounds more acidic than it are $HCOOH$ (no $+I$ effect), $ClCH_2COOH, FCH_2COOH, NC-CH_2COOH, CCl_3COOH$ (all contain powerful $-I$ groups), and $C_6H_5COOH$ (benzoic acid has a stronger Ka than acetic acid). Only propanoic acid ($CH_3CH_2COOH$) is weaker due to a larger $+I$ group.

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