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The question is :

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Now, this is what I have done :

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So I dont know how to proceed to the final product. In some book they tell we need to break the cyclopropane to get the desirable answer but how ?

Please help.

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2 Answers 2

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This paper (JCS Perkin 1 (1975) 1638-40) reports that dichlorocarbene reacts with cyclopentadiene at 180C to give chlorobenzene. The strained cyclopropyl ring opens to give insertion with loss of chloride anion. I see no reason why dibromocarbene should give a different outcome, so the answer is C.

See this SE answer How does chloroform react with cyclopentadiene in base?

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Here OTs being a good leaving group will be eliminated by alc KOH making cyclopent-1,3-diene, t-BuO- being a solvent will make :CBr2 which will act as a Base and abstract proton from C5. Hence option D will be the answer.

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    $\begingroup$ Do you have a literature reference for this? $\endgroup$
    – Waylander
    Commented Jan 15 at 9:23

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