1.

An organic compound (A) of molecular formula C_(3)H_(8)O gives turbidity within 5-10 min on reaction with anhydrous ZnCl_(2)//HCl. Compound (A) on treatment with sodium hypochlorite gives a carbonyl compound (B) with on further chlorination gives compound (C) of molecular formula C_(3)H_(3)OCl_(3). Identify (A),( B) and (C). Explain the reaction.

Answer»

Solution :(i) (A) that gives turbidity WITHIN 5-10 min on reaction with anhydrous `ZnCl_(2)//HCL` means it must be secondary alcohol.
`CH_(3)-underset(OH)underset(|)(CH)-CH_(3) overset("anhydrous ZnCl_(2)//HCl) to CH_(3)-underset(Cl) underset(|)(CH-CH_(3)) + HCl`
(ii) Iso PROPYL alcohol on treatment with SODIUM hypochlorite, undergoes oxidation to give acetone compound (B).
`underset(A)underset(OH)underset(|)(CH)-CH_(3) overset((O)) to underset(B)underset(O)underset(||)C-CH_(3)`
(iii) Acetone on treatment with chlorine gives trichloro acetone and it is (C).
`underset(B)underset((O))underset(||)C-CH_(3) + 3Cl_(2) to underset((C))underset(O)underset(||)C-CH_(3) + 3HCl`


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