State oxidized to an optically inactive dicarboxylic acid c

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Compound A, C6H12O2, was found to be optically active, and it was slowly oxidized to an optically active carboxylic acid B, C6H12O3, by Ag(NH3)2. Oxidation of A by anhydrous CrO3 gave an optically inactive compound D that reacted with Zn amalgam/HCl to give 3-methylpentane. With aqueous H2CrO4, compound A was oxidized to an optically inactive dicarboxylic acid C, C6H10O4. Give structures for compounds A, B, and C; do not specify stereochemistry.

Reference no: EM13229561

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