In: Chemistry
Compound A has the molecular formula C11H12O. It gives a positive reaction with 2,4‐dinitrophenylhydrazine, but a negative result with a Tollens’ test. Treating compound A with LiAlH4 followed by dilute acid produces compound B, C11H14O, which can be resolved into enantiomers. When optically active compound B is oxidized by K2Cr2O7/H2SO4 solution, an optically inactive sample of compound A is produced. Heating compound A in basic hydrazine solution gives compound C, C11H14. Compound C does not decolorize a solution of bromine in CCl4, but heating compound C in basic KMnO4 solution produces compound D: Give possible structures for compounds A, B, and C. Explain how you deduced those structures.