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Compound A of molecular formula C_(2)H_(8) is treated with chlorine and then with NaOH to get compound B of molecular formula. C_(2)H_(8)O. B on oxidation by acidified K_(2)Cr_(2)O_(7) gives compound C of molecular formula C_(7)H_(6)O. Compound C on treatment with 50% caustic soda gives the compound B and also D. Find A,B,C and D. Explain the reactions. |
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Answer» Solution :(i) An organic compound A is identified as toluene from its molecular formula. (ii) (A) on reaction with chlorine gives benzyl chloride whicih on further reactions with NaOH produces (B). `C_(6)H_(5)-CH_(3) overset(Cl_(2))UNDERSET(-HCl) to C_(6)H_(5)CH_(2)Cl overset(NaOH)underset(-NaCl) to underset((B)) (C_(6)H_(5)CH_(2)OH` (III) B on oxidation with ACIDIFIED `K_(2)Cr_(2)O_(7)` gives (C). `C_(6)H_(5)CH_(2)OH overset(K_(2)Cr_(2)O_(7)//H^(+))underset(NaOH) to underset((C))(C^(6)H^(5)CHO) + H_(2)O` (iv) Benzaldehyde on treatment with 50% caustic soda gives (D) and (B). `underset((C))(C_(6)H_(5)CHO) + C_(6)H_(5)CHO overset(50%)underset(NaOH) to underset(B)(C_(6)H_(5)CH_(2)OH) + underset((D))(C_(6)H_(5)COOH)` 
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