CBSE Class 12 Chemistry 2018 Solved Paper

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Question : 9
Total: 26
How do you convert the following ?
(a) Ethanal to Propanone
(b) Toluene to Benzoic acid
OR
Account for the following:
(a) Aromatic carboxylic acids do not undergo Friedel-Crafts reaction.
(b) pKa value of 4-nitrobenzoic acid is lower than that of benzoic acid.
Solution:  
(a) CH3CHO
(i) CH3MgBr, Dryether
(ii) H2OH+
CH3CH(OH)CH3
CrO3
CH3COCH3
OR
(a) because the carboxyl group is deactivating and the catalyst aluminium chloride (Lewis acid) gets bonded to the carboxyl group
(b) Nitro group is an electron withdrawing group (-I effect) so it stabilises the carboxylate anion and strengthens the acid/ due to the presence of an electron withdrawing nitro group (-I effect).
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