My attempt is illustrated below:
or
Which of these methods is most viable?
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3
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3$\begingroup$ You need acid (and probably heat) present for the top reaction to give elimination. It it also possible with the correct choice of catalyst to reduce the alkyl halide by hydrogenation. $\endgroup$– WaylanderJun 23, 2021 at 6:56
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1$\begingroup$ For the last step in both reactions, ensure enough pressure of hydrogen, literally. Otherwise, with cyclo-hexa-1,3-diene already in hand, you might drop into the formation of benzene. $\endgroup$– ButtonwoodJun 24, 2021 at 6:30
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$\begingroup$ you can directly get your desired product with $\ce{H2 + Ni + \Delta}$ $\endgroup$– napstablookJun 25, 2021 at 5:44
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