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Rank these acids according to their expected pKa values?

ClCH2CH2COOHCH3CH2COOHCICH2COOHCI2CHCOOH Thanks!

3 Answers

From low pKa (stronger acid) to high pKa (weaker acid):CI2CHCOOH CICH2COOH ClCH2CH2COOHCH3CH2COOHThe explanation is the inductive (electron-withdrawing) effect of substituents on the carbon alpha to the carboxyl group.http://www2.chemistry.msu.edu/faculty/reusch/VirtT...(Scroll down to the section titled, "2. Acidity of Carboxylic Acids")... Show More
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