Chapter 8, Problem 52P

Deduce the structures of compounds A, B, and C, which all have the formula $C_6{H}_{10}$. As you read the information chat follows, draw reaction flowcharts (roadmaps) like those in Problems 8.24 and 8.49. This approach will help you solve the problem. All three compounds rapidly decolorize bromine; all three are soluble in cold concentrated sulfuric acid. Compound A has an absorption in its IR spectrum at about 3300 $c{m}^{-1}$, but compounds Band C do not. Compounds A and B both yield hexane when they are treated with excess hydrogen in the presence of a platinum catalyst. Under these conditions C absorbs only one molar equivalent of hydrogen and gives a product with the formula $C_6{H}_{12}$ When A is oxidized with hot basic $KMn{O}_4$, and the resulting solution acidified,

the only organic product that can be isolated is . Similar oxidation of B gives only , and similar treatment of C gives only .