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Write Brief Answer · Q19

Q.Complete the following reactions:

(i) Phenol --C6H5COCl/OH---> A --Nitration--> B (major product)
(ii) C6H5-CH2-CH(OH)-CH(CH3)2 --Conc. H2SO4--> ? (identify the major product)
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Step 1. (i) Phenol + C6H5COCl/OH- (Schotten-Baumann benzoylation) gives A = phenyl benzoate, C6H5-O-CO-C6H5.

Step 2. Phenyl benzoate has two aromatic rings: the phenol-derived ring (attached to the ester oxygen, still weakly activated/ortho-para-directing) and the benzoyl-derived ring (attached to the carbonyl, deactivated/meta-directing, like any aryl ester carbonyl). Nitration therefore occurs preferentially on the more activated, phenol-derived ring, predominantly at the position PARA to the ester oxygen, giving B (major) = 4-nitrophenyl benzoate.

Step 3. (ii) C6H5-CH2-CH(OH)-CH(CH3)2 with conc. H2SO4 undergoes acid-catalysed (E1) dehydration; loss of water from the secondary -OH carbon can lose a beta-hydrogen from EITHER the benzylic side (C1, next to the phenyl ring) or the isopropyl side (C3). …

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