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An organic compound A (C(4)H(10)O) react...

An organic compound A `(C_(4)H_(10)O`) reacts with HI giving a compound B(`C_(4)H_(9)l`), which on reduction gives n-butane. On oxidation 'A' gives a compound `C(C_(4)H_(8)O`) and then an acid `D(C_(4)H_(8)O_(2))`.
Deduce the structures of A, B, C and D and mention their IUPAC names.

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A hydrocarbon A(C_(4)H_(8)) on reaction with HCl gives a compound 'B' (C_(4)H_(9)Cl) which on reaction with 1 mole of NH_3 gives compound 'C' (C_(4)H_(11)N) . On reacting with NaN02 and HC1 followed by the'treatment with water, compound 'C yields an optically active alcohol, 'D'. Ozonolysis of 'A gives 2 moles of acetaldehyde. Identify compounds 'A to 'D'. Explain the reactions involved.

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