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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

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Number of `C` atoms in (A),(B), and (C)=6. So combine the products of ozonolysis to get `6C-`atom compound.
i. `(2C) ` is combined with `(iv).(4C)` to get one compound `(B)`.
ii. (3C) is combined with (iii).(3C) to get another compound `(C)`.

Since, `(B)` and `(C)` are obtained from chloride `(A)`, thus `(A)` should be `:`

Hallide cannot be `(I)` since on dehydrohalogenation with alc. `KOH` it will give only one product , but `(II)` will give two products. Thus halide is `(II)`.
Reations `:`
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