1. Tardigrade
  2. Question
  3. Chemistry
  4. Catalytic hydrogenation of compound ‘X’ (C10H14) gives butyl cyclohexane. Treatment of ‘X’ with Cu(NH3)2+ gives no precipitate but does after treatment with hot NaNH2. When ‘X’ is first reacted with H2/Ni2B and then oxidatively ozonized, a non resolvable compound is formed. The organic compound ‘X’ is

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Q. Catalytic hydrogenation of compound ‘$X$’ $(C_{10}H_{14})$ gives butyl cyclohexane. Treatment of ‘$X$’ with $Cu(NH_3)_2^+$ gives no precipitate but does after treatment with hot $NaNH_2$. When ‘$X$’ is first reacted with $H_2/Ni_2B$ and then oxidatively ozonized, a non resolvable compound is formed. The organic compound ‘$X$’ is

Hydrocarbons

Solution:

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$Cu(NH_3)_2^+$ gives no ppt. $\Rightarrow $ no terminal triple bond but gives ppt. with $Cu(NH_3)_2^+$ on treatment of $NH_2^-$
$\Rightarrow $ there is internal triple bond.
• In the ring triple bond is not possible
• $H_2/Ni_2B$ 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
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