Chapter 14, Problem 32P

Deduce the structure of each of the following compounds on the basis of their $\text{H}\text{NMR}$

Spectra and molecular formulas:

${\text{C}}_{\text{8}}{\text{H}}_{\text{10}}$

$\delta \text{ 1}\text{.2 (triplet, 3H)}$

$\delta \text{ 2}\text{.6 (quartet, 2H)}$

$\delta \text{ 7}\text{.1 (broad singlet, 5H)}$

${\text{C}}_{\text{10}}{\text{H}}_{\text{14}}$

$\delta \text{ 1}\text{.3 (singlet, 9H)}$

$\delta \text{ 7}\text{.0 to 7}\text{.5 (multiplet, 5H)}$

${\text{C}}_{\text{6}}{\text{H}}_{\text{14}}$

$\delta \text{ 0}\text{.8 (doublet, 12H)}$

$\delta \text{ 1}\text{.4 (septet, 2H)}$

${\text{C}}_{\text{6}}{\text{H}}_{\text{12}}$

$\delta \text{ 0}\text{.9 (triplet, 3H)}$

$\delta \text{ 1}\text{.6 (singlet, 3H)}$

$\delta \text{ 1}\text{.7 (singlet, 3H)}$

$\delta \text{ 2}\text{.0 (quintet, 2H)}$

$\delta \text{ 5}\text{.1 (triplet, 1H)}$

${\text{C}}_{\text{4}}{\text{H}}_{\text{6}}{\text{Cl}}_{\text{4}}$

$\delta \text{ 3}\text{.9 (doublet, 4H)}$

$\delta \text{ 4}\text{.6 (triplet, 2H)}$

${\text{C}}_{\text{4}}{\text{H}}_{\text{6}}{\text{Cl}}_{\text{2}}$

$\delta \text{ 2}\text{.2 (singlet, 3H)}$

$\delta \text{ 4}\text{.1 (doublet, 2H)}$

$\delta \text{ 5}\text{.7 (triplet, 1H)}$

${\text{C}}_{\text{3}}{\text{H}}_{\text{7}}\text{ClO}$

$\delta \text{ 2}\text{.0 (quintet, 2H)}$

$\delta \text{ 2}\text{.8 (singlet, 1H)}$

$\delta \text{ 3}\text{.7 (triplet, 2H)}$

$\delta \text{ 3}\text{.8 (triplet, 2H)}$

${\text{C}}_{\text{14}}{\text{H}}_{\text{14}}$

$\delta \text{ 2}\text{.9 (singlet, 4H)}$

$\delta \text{ 7}\text{.1 (broad singlet, 10H)}$