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NCERT Class XII Chemistry
Chapter - Aldehydes, Ketones and Carboxylic Acids
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Question : 28 of 28
Marks: +1, -0
Which acid of each pair shown here would you expect to be stronger ?
(i) CH3CO2HCH_3CO_2H or CH2FCO2HCH_2FCO_2H
(ii) CH2FCO2HCH_2FCO_2H or CH2ClCO2HCH_2ClCO_2H
(iii) CH2FCH2CH2CO2HCH_2FCH_2CH_2CO_2H or CH3CHFCH2CO2HCH_3CHFCH_2CO_2H
Solution:  
(i) H2CFCOOHH_2CFCOOH will be stronger of the two. The presence of electronegative F atom at the α-C causes electron withdrawal from the COOH and facilitates the release of H+^{+}.
(ii) CH2FCO2HCH_2FCO_2H is a stronger acid for the same reason as stated above. F is more electronegative than Cl, so it withdraws electrons from the carboxyl group to a greater extent.
(iii) CH3CHFCH2COOHCH_3CHFCH_2COOH is stronger. Although both the given acids have F atom in them, it is the proximity of F in CH3CHFCH2COOHCH_3CHFCH_2COOH to the COOH group which makes it more acidic.
(iv)
is more acidic due to the presence of electron withdrawing CF3 group in it.
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