Hydrocarbons 2 Question 70
75. A white precipitate was formed slowly when silver nitrate was added to compound $A$ with molecular formula $\mathrm{C}{6} \mathrm{H}{13} \mathrm{Cl}$. Compound $A$ on treatment with hot alcoholic potassium hydroxide gave a mixture of two isomeric alkenes $B$ and $C$, having formula $\mathrm{C}{6} \mathrm{H}{12}$. The mixture of $B$ and $C$, on ozonolysis, furnished four compounds
(i) $\mathrm{CH}{3} \mathrm{CHO}$ (ii) $\mathrm{C}{2} \mathrm{H}_{5} \mathrm{CHO}$
(iii) $\mathrm{CH}{3} \mathrm{COCH}{3}$
What are the structures of $A, B$ and $C$ ?
$(1986,4 \mathrm{M})$
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Solution:
- The alkenes are :
Since, both alkenes I and II are obtained by $\beta$-elimination of same halides, the halides must be :
(A)
