In the laboratories of the firm “Halides ‘R’ Us,” a compound A has been found in a vial labeled only “achiral alkyl halide C₁₀H₁₇Br.” The management feels that the compound might be useful as a pesticide, but they need to know its structure. You have been called in as a consultant at a handsome fee. Compound A, when treated with KOH in warm ethanol, yields two compounds (B and C), each with the molecular formula C₁₀H₁₆. Compound A rapidly reacts in aqueous ethanol to give an acidic solution, which, in turn, gives a precipitate of AgBr when tested with AgNO₃ solution. Ozonolysis of A followed by treatment with (CH₃)₂S affords (CH₃)₂C = O (acetone) as one of the products plus unidentified halogen-containing material.

Catalytic hydrogenation of either B or C gives a mixture of both trans- and cis-1-isopropyl-4-methylcyclohexane. Compound A reacts with one equivalent of Br₂ to give a mixture of two separable compounds, D and E, both of which can be shown to be achiral compounds. Finally, ozonolysis of compound B followed by treatment with aqueous H₂O₂ gives acetone and the diketone F.

Propose structures for compounds A through E that best fit the data (and collect your fee).

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F