Identify A in the given chemical reaction.
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The Correct Option is D
Solution and Explanation
(i) \(\mathrm{HCHO, NaOH}\): crossed Cannizzaro reaction. Formaldehyde is the better hydride donor and is oxidised to formate; the aromatic aldehyde is reduced to 4-methoxybenzyl alcohol, \(\mathrm{CH_3O-C_6H_4-CH_2OH}\).
(ii) \(\mathrm{CH_3CH_2Br, NaH, DMF}\): NaH forms the alkoxide, which gives \(\mathrm{CH_3O-C_6H_4-CH_2-OC_2H_5}\) by Williamson synthesis.
(iii) \(\mathrm{HI, \Delta}\): the aryl methyl ether cleaves to the phenol + \(\mathrm{CH_3I}\) (the aryl C-O bond is not broken), and the benzylic ether cleaves to the benzylic iodide + \(\mathrm{C_2H_5OH}\).
Product A: \(\mathrm{HO-C_6H_4-CH_2I}\) (4-hydroxybenzyl iodide), option (4).
Answer: (4) 4-hydroxybenzyl iodide, \(\mathrm{HO-C_6H_4-CH_2I}\)
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