Hydrocarbons 2 Question 67
72. Give the structures of $A, B$ and $C$ (explanation are not required)
(i) $A\left(\mathrm{C}{4} \mathrm{H}{8}\right)$ which adds on $\mathrm{HBr}$ in the presence and in the absence of peroxide to give same product.
(ii) $B\left(\mathrm{C}{4} \mathrm{H}{8}\right)$ which when treated with $\mathrm{H}{2} \mathrm{O} / \mathrm{H}{2} \mathrm{SO}{4}$ gives $\mathrm{C}{4} \mathrm{H}_{10} \mathrm{O}$ which cannot be resolved into optical isomers.
(iii) $\mathrm{C}\left(\mathrm{C}{6} \mathrm{H}{12}\right)$, an optically active hydrocarbon which on catalytic hydrogenation gives an optically inactive compound $\mathrm{C}{6} \mathrm{H}{14}$.
$(1993,1 \mathrm{M} \times 3=3 \mathrm{M})$
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Solution:
- (i) $A$ must be a symmetrical alkene :
(ii)
(iii)
has one chiral carbon
