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acid base - electron-withdrawing group on the 1 st carbon...

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MCAT question: Why does ClCH 2 CH 2 CH 2 COOH (M1) have a greater pKa than ClCH 2 COOH (M2)? A. M1 has a higher molecular weight than M2 B. M1 has a lower molecular weight than M2 C. M1 has an electron-withdrawing group on the 3 rd carbon from the COOH while M2 has an
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Unformatted text preview: electron-withdrawing group on the 1 st carbon from the COOH D. M1 is a longer chain than M2 Since M1 has a greater pKa, the stronger acid of the two is M2. This is due to the presence of an EWG (the Cl substituent) that is closer to the COOH....
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