Compound A (C₈H₁₅Cl) exists as a racemic form. Compound A does not react with either Br₂ or dilute aqueous KMnO₄. When A is treated with magnesium in dry ether followed by aqueous acid and the mixture is separated by gas chromatography, two fractions, B and C, are obtained. The components of both fractions have the formula C₈H₁₆. Fraction B consists of a racemic form and can be resolved. Fraction C cannot be resolved. Treating A with sodium ethoxide in ethanol converts A into D (C₈H₁₄). Hydrogenation of D using a platinum catalyst yields C. Ozonolysis of D followed by treatment with dimethyl sulfide yields

Propose structures for A, B, C, and D, including, where appropriate, their stereochemistry

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