Your friend of Question 160 still needs your help. A week later a low-melting solid, compound A, was isolated, which combustion analysis showed had composition C9H10O. The substance gave a precipitate when treated with 2,4-dinitrophenylhydrazine solution. Furthermore, when reacted with iodoform reagent, a yellow precipitate of CHI3 was observed. Acidification of the alkaline solution from the iodoform test produced a solid material, compound B. Reduction of compound A with LiAlH4 gave compound C (C9H12O). Compound C also gave compound B when treated with iodoform reagent.Vigorous oxidation of compound A, B, or C with sodium dichromate–sulfuric acid solution gave an acid having an mp 121–122°C. Your friend needs your assistance in determining the structures for compounds A, B, and C. Can you identify the three compounds?
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