Identify compounds A, B, and C from the following information. (a) Compound A, C8H10O

Chapter 18, Problem 18.52

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Identify compounds A, B, and C from the following information. (a) Compound A, C8H10O, is insoluble in water but soluble in aqueous NaOH solution, and yields 3,5-dimethylcyclohexanol when hydrogenated over a nickel catalyst at high pressure. (b) Aromatic compound B, C8H10O, is insoluble in both water and aqueous NaOH solution. When treated successively with concentrated HBr, then Mg in THF, then water, it gives p-xylene. (c) Compound C, C9H12O, is insoluble in water and in NaOH solution, but reacts with concentrated HBr and heat to give m-cresol and a volatile alkyl bromide.

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