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Q.

The compound from the following with highest  pka is  

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a

C6H5CH2COOH

b

HCOOH

c

C6H5COOH

d

CH3COOH

answer is C.

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Detailed Solution

All aromatic acids are more acidic than aliphatic acids except HCOOH.

In C6H5COOH,  C6H5 group show +M effect and –I effect due to sp2 hybridized carbon atoms of benzene ring.

Question Image
Question Image

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 > CH3COOH

Comparing C6H5COOH, C6H5CH2COOH, CH3COOH

C6H5COOH > C6H5CH2COOH > CH3COOH

Question Image

HCOOH > C6H5COOH > C6H5CH2COOH  > CH3COOH

pka of HCOOH < C6H5COOH < C6H5CH2COOH  <CH3COOH

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