A hydrocarbon of unknown structure has the formula $C_{8} H_{10}$ . On catalytic hydrogenation over the Lindlar catalyst, 1 equivalent of $H_{2}$ is absorbed. On hydrogenation over a palladium catalyst, 3 equivalents of $H_{2}$ are absorbed. Suggest several structures:

The number of structures < 2

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The number of structures < 3

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The number of structures < 4

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None of the above

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Solution

The correct option is D None of the above
Start by calculating the degree of unsaturation or the Double bond equivalents:

Calculate DBE = { C + 1 - (H/2) + (N/2) }
= 8 + 1 - 5
= 4

There has to be exactly one triple bond (which takes of 2 out of 3 $π$ bonds).
Total DBE = 4; And there are exactly 3 $π$ bonds of which 2 has been accounted for.

So definitely, there has to be a ring. Some of the possible structures are:

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A hydrocarbon of unknown structure has the formula $C_{8} H_{10}$ . On catalytic hydrogenation over the Lindlar catalyst, 1 equivalent of $H_{2}$ is absorbed. On hydrogenation over a palladium catalyst, 3 equivalents of $H_{2}$ are absorbed. Suggest several structures:

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A hydrocarbon of unknown structure has the formula C8H10. On catalytic hydrogenation over the Lindlar catalyst, 1 equivalent of H2 is absorbed. On hydrogenation over a palladium catalyst, 3 equivalents of H2 are absorbed. Suggest several structures:

A hydrocarbon of unknown structure has the formula $C_{8} H_{10}$ . On catalytic hydrogenation over the Lindlar catalyst, 1 equivalent of $H_{2}$ is absorbed. On hydrogenation over a palladium catalyst, 3 equivalents of $H_{2}$ are absorbed. Suggest several structures: