Orgoreview

Two compounds, A and B, with the molecular formula C₇H₁₃Br are chiral and are diastereomers of each other. Treatment of A and B with C₂H₅O^Θ produces two alkenes, C and D, with the molecular formula C₇H₁₂. Compound C is chiral but D is not chiral. Treatment of both C and D with H₂/Pd gives the compound methyl cyclohexane.

Give structures for A, B, C and D consistent with this data.