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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

(A) forms slowly a white silver nitrate, hence, it should be a secondary alkyl halide. Since, each alkene has six carbon stoms `(C_6H_12)`, so `CH_3CHO` and `CH_3-underset(CH_3)underset(|)CH-CHO` must result form one alkene and `C_2H_5CHO` and `CH_3COCH_3` from other alkene, Thus, the structure of two alkenes are:

The structure of secondary alkyl halide which yields (B) and (C) alkenes on treatment with alc. `KOH` is:
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C_(6)H_(5)CH=underset(CH_(3))underset(|)C-CHO

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Knowledge Check

  • Name the compound CH_(3)CH(C_(2)H_(5))CH(CHO)CH_(3)

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