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  4. A hydrocarbon with molecular formula C6H8 is chiral but upon catalytic hydrogenation gives achiral hydrocarbon of molar mass 8 6. Which of the following could be the starting compound?

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Q. A hydrocarbon with molecular formula $C_{6}H_{8}$ is chiral but upon catalytic hydrogenation gives achiral hydrocarbon of molar mass $8 6.$ Which of the following could be the starting compound?

Organic Chemistry – Some Basic Principles and Techniques

Solution:

Molar mass $86$ correspond to $C_{6}H_{14}$, i.e. starting compound has not ring structure.
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