Q.
The compound from the following with highest pka is
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a
HCOOH
b
C6H5COOH
c
CH3COOH
d
C6H5CH2COOH
answer is C.
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Detailed Solution
All aromatic acids are more acidic than aliphatic acids except HCOOH.In C6H5–COOH, –C6H5 group show +M effect and –I effect due to sp2 hybridized carbon atoms of benzene ring.– I effect is due to sp2 carbons –I effect in this compound dominates +M effect.∴Benzoic acid is more acidic than all aliphatic acids except HCOOH∴HCOOH > C6H5COOH > CH3COOHComparing C6H5COOH, C6H5CH2COOH, CH3COOHC6H5COOH > C6H5CH2COOH > CH3COOH∴HCOOH > C6H5COOH > C6H5CH2COOH > CH3COOHpka of HCOOH < C6H5COOH < C6H5CH2COOH
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