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Elimination reactions by the E2 mechanism are facilitated when the nucleofuge and H on adjacent C atoms can achieve an antiperiplanar relationship. This is only possible in chair trans-1,2-dibromocyclohexane when both Br atoms are axial. The Br at C1 can then be eliminated with a trans axial H on C6 from this (unfavourable) conformation, and the Br at C2 can be eliminated with a trans axial H on C3. Either way, the product is 3-bromocyclohexene which can then undergo a further E2 elimination to give cyclohexa-1,3-diene.
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