Chapter 15, Problem 52P

Propose a structure consistent with each set of data.

a. ${\text{C}}_{\text{10}}{\text{H}}_{\text{14}}:\text{IR}\text{absorptions}\text{at}\text{3150}-2850,1600,\text{and}\text{1500}{\text{cm}}^{-1}$

b. ${\text{C}}_9{\text{H}}_{\text{12}}:{}^{13}\text{C}\text{NMR}\text{signals}\text{at}21,127,\text{and}\text{138}\text{ppm}$

c. ${\text{C}}_8{\text{H}}_{\text{10}}:\text{IR}\text{absorptions}\text{at}\text{3108}-2875,1606,\text{and}\text{1496}{\text{cm}}^{-1}$