Question

Catalytic hydrogenation of compound ‘$X$’ $(C_{10}{H}_{14})$ 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 $H_2/N{i}_{2}B$ and then oxidatively ozonized, a non resolvable compound is formed. The organic compound ‘$X$’ is

• A.
• B.
• C.
• D.

Answer 1

Answer: (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.
• In the ring triple bond is not possible
• $H_2/N{i}_{2}B$ treatment reduces triple bond to double bond. Now possible options are (b), (c) and (d)
• Oxidative ozonolysis gives non-resolvable compound. So only (d) is possible