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Q.

Catalytic hydrogenation of compound ‘X’ C10H14 gives butyl cyclohexane. Treatment of ‘X’ with CuNH32+ 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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a

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b

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c

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d

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answer is D.

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Detailed Solution

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CuNH32+ gives no ppt.  no terminal triple bond but gives ppt. with CuNH32+ on treatment of NH2-

 In the ring triple bond is not possible

  • H2/Ni2B treatment reduces triple bond to double bond. Now possible options are 2, 3 and 4
  • Oxidative ozonolysis gives non-resolvable compound. So only 4 is possible
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