Chemistry Homework Solutions
Problem
#44673

Identifying 3 unknown compounds

A low-melting solid (compound A) was isolated, and combustion analysis showed it had compisition 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). This compound C also gave compound B when treated with iodoform reagent. Vigorous oxidation of A, B or C with sodium dichromate-sulfuric acid solution gave an acid having a melting point of 121 - 122 degrees C. Can you identify the ststructures and names for compounds A, B, and C?

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