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Two isomeric compounds A and B having molecular formula C_(4)H_(11)N, both lose N_(2) on treatment with HNO_(2) and gives compound C and D, respectively. C is resistant to oxidation but immediately responds to Lucas reagent, whereas 'D' responds to Lucas reagent after 5 minutes and gives a positive iodoform test. Identify A and B. |
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Answer» Solution :The following REACTIONS lead to the identification of A and B : `CH_(3)-underset(underset(underset((B))(NH_(2)))(|))(CH)-CH_(2)-CH_(3)+HNO_(2) rarr CH_(3)-underset(underset(underset((D))(OH))(|))(CH)-CH_(2)-CH_(3)+N_(2)+H_(2)O` `CH_(3)-underset(underset(underset((A))(NH_(2)))(|))overset(overset(CH_(3))(|))(C)-CH_(3)+HNO_(2) rarr CH_(3)-underset(underset(underset((C))(OH))(|))overset(overset(CH_(3))(|))(C)-CH_(3)+N_(2)+H_(2)O` `CH_(3)-underset(underset(underset((C))(OH))(|))overset(overset(CH_(3))(|))(C)-CH_(3)+conc.HCl overset(ZnCl_(2)(Anhyd.))(rarr)CH_(3)-underset(underset(Cl)(|))overset(overset(CH_(3))(|))(C)-CH_(3)+H_(2)O` .C. is resistant to oxidation because tertiary alcohols do not undergo oxidation. It gives turbidity immediately with LUCAS reagent. .D. responds to Lucas reagent test within 5 MINUTES because it is secondary alcohol and turbidity appears after 5 minutes. `CH_(3)-underset(underset(underset("Butan-2-ol")(OH))(|))(CH)-CH_(2)-CH_(3)+underset(conc)(HCl) overset(ZnCl_(2)(Anhyd.))(rarr)CH_(3)-underset(underset(underset("2-Chlorobutane")(Cl))(|))(CH)-CH_(2)-CH_(3)` `CH_(3)-underset(underset(underset("(D)Butan-2-ol")(OH))(|))(CH)-CH_(2)-CH_(3) underset((NaOI))overset(I_(2)//NaOH)(rarr)CH_(3)-underset(underset(underset("2-Butanone")(O))(||))(C)-CH_(2)-CH_(3) overset(I_(2)//NaOH)(rarr)underset("Iodoform")(CHI_(3))+underset("Sodium propanoate")(CH_(3)CH_(2)COONa)+3NaI+2H_(2)O` |
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