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$\begingroup$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.$\endgroup$
$\begingroup$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.$\endgroup$