Compound A, C₁₁H₁₂O, which gave a negative Tollens test, was treated with LiAlH₄, followed by dilute acid, to give compound B, which could be resolved into enantiomers.

When optically active B was treated with CrO₃ in pyridine, an optically inactive sample of A was obtained.

Heating A with hydrazine in base gave hydrocarbon C, which, when heated with alkaline KMnO₄, gave carboxylic acid D. Identify all of the compounds and explain your reasoning.

Transcribed Image Text:

HO₂C. HO₂C D CO₂H CO₂H