Question

Catalytic hydrogenation of compound ‘X’ $\left(C_{10}{H}_{14}\right)$ gives butyl cyclohexane. Treatment of ‘X’ with $Cu(N{H}_3{)}_2^{+}$ gives no precipitate but does after treatment with hot $NaN{H}_2$. When ‘X’ is first reacted with $\frac{H_2}{N{i}_{2}B}$ and then oxidatively ozonized, a non resolvable compound is formed. The organic compound ‘X’ is -

• A.
• B.
• C.
• D.

Answer 1

The correct option is D


$Cu(N{H}_3{)}_2^{+}$ gives no ppt. $\Rightarrow$ no terminal triple bond But gives ppt with $Cu(N{H}_3{)}_2^{+}$ on treatment of $N{H}_2^{-}$
$\Rightarrow$ there is internal triple bond.
a) In the ring triple bond is not possible
b) $\frac{H_2}{N{i}_{2}B}$ treatment reduces triple bond to double bond. Now possible options are (B), (C) and (D)
c) Oxidative ozonolysis gives non-resolvable compound. So only (D) is possible