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) ‌H2O∕H+
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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