Chapter 16, Problem 36P

Give structures for compounds A–E.

Cyclohexanol $\begin{array}{l}\underset{acetone}{\overset{H_{2}Cr{O}_4}{\to }}A\left(C_6{H}_{10}O\right)\underset{H_3{O}^{+}}{\overset{\left(1\right)C{H}_{3}MgI}{\to }}B\left(C_7{H}_{14}O\right)\underset{heat}{\overset{HA}{\to }}C\left(C_7{H}_{12}\right)\underset{\left(2\right)M{e}_{2}S}{\overset{\left(1\right)O_3}{\to }}\\ D\left(C_7{H}_{12}{O}_2\right)\underset{\left(2\right)H_3{O}^{+}}{\overset{\left(1\right)A{g}_{2}O,H{O}^{-}}{\to }}E\left(C_7{H}_{12}{O}_3\right)\end{array}$