A: Compound A is 2-methylcyclohexanol
B: Compound B is 2-methylcyclohexanone
C: Compound C is 2-methylcyclohexyl acetate
D: Compound D is β-methylglutaric acid (3-methylpentanedioic acid)
An optically active compound A, C6H10O2, when dissolved in NaOH solution, consumed one equivalent of base. On acidification, compound A was slowly regenerated. Treatment of A with LiAlH4 in ether followed by protonolysis gave an optically inactive compound B that reacted with acetic anhydride to give an acetate diester derivative C. Compound B was oxidized by aqueous chromic acid to β-methylglutaric acid (3-methylpentanedioic acid), D. Identify compounds A, B, and C; do not specify stereochemistry.
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