Explain when optically active b was treated

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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 compounds A, B, and C.

Reference no: EM13261233

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