A compound A with molecular formula \(\mathrm{C_{10}H_{13}Cl}\), gives a white precipitate on adding silver nitrate solution. A on reacting with alcoholic KOH gives compound B as the main product. B on ozonolysis, gives C and D. C gives Cannizzaro reaction, but not aldol condensation. D gives aldol condensation, but not Cannizzaro reaction. A is
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The Correct Option is B
Solution and Explanation
Option (2) is \(\mathrm{C_6H_5CH_2-C(CH_3)_2Cl}\). With alcoholic KOH it eliminates HCl to give B = \(\mathrm{C_6H_5CH=C(CH_3)_2}\).
Ozonolysis of B gives \(\mathrm{C_6H_5CHO}\) (C; no alpha-H, so Cannizzaro but no aldol) and \(\mathrm{CH_3COCH_3}\) (D; has alpha-H and no CHO, so aldol but no Cannizzaro).
Option (1) would give \(\mathrm{C_6H_5CH_2CHO}\) + \(\mathrm{CH_3CHO}\), both of which show aldol, so it fails.
Answer: (2) \(\mathrm{C_6H_5-CH_2-C(CH_3)_2-Cl}\)
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