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A white precipitate was formed slowly wh...

A white precipitate was formed slowly when silver nitrate was added to compound `(A)` with molecular formula `C_(6)H_(13)Cl`.Compound `(A)` on treatment with hot alcoholic potassium hydroxide gave a misture of two isomeric alkenes `(B)` and `(C)`, havinig the formuls `C_(6)H_(12)`. The mixture of `(B)` and `(C)`, on ozonolsis, furnished four compounds.
i. `CH_(3)CHO`,ii `C_(2)H_(5)CHO`
iii. `CH_(3)COCH_(3)`,(iv) `CH_(3)-underset(CH_(3))underset(|)(CH)-CHO`
What are the structures of (A),(B)and (C) ?

Text Solution

Verified by Experts

From the molecular formula it is clear that compound is saturated alkyl halide. On treatment with alcoholic KOH, H-forms mixture of two normal alkenes. It means halogen is not at terminal carbon and the alkyl chloride contains long chain of carbon atoms. two possible alkene mixtures.

But the second mixture of alkenes cannot give four different compounds on ozonolysis. hence the structure and reaction are:
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