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A hydrocarbon A(C(4)H(8)) on reaction w...

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.

Text Solution

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Addition of HCl to compound CA. shows that compound .A. is alkene because compound .B. is:
`C_(4)H_(9)Cl`
(ii) Compound .B. reacts with `NH_3`, to form amine .C..
`C_(4)H_(8)overset(HCl) to underset(B)(C_(4)H_(9)Cl) overset(NH_(3)) to underset(C )(C_(4)H_(11)N` or `C_(4)H_(9)NH_(2)`
(iii) .C gives diazonium salt with `NaNO_(2)//HCl`, which yields an optically active alcohol. So, .C is an aliphatic amine.
(iv) .A. on ozonolysis produces 2 moles of `CH_(3)CHO`.
So, .A. is `CH_(3) - CH =CH -CH_(3)` (but-2-ene) (1)
Therefore, overall reaction sequence look like:

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