Chapter 14, Problem 39P

Identify each of the ${\text{C}}_{\text{4}}{\text{H}}_{\text{10}}\text{O}$ isomers on the basis of their $\text{C}$

NMR spectra:

$\text{δ 18}\text{.9 }\left({\text{CH}}_{\text{3}}\right)$ (two carbons)

$\text{δ 30}\text{.8 }\left(\text{CH}\right)$

(one carbon)

$\text{δ 69}\text{.4 }\left({\text{CH}}_2\right)$

(one carbon)

$\text{δ 10}\text{.0 }\left({\text{CH}}_{\text{3}}\right)$

$\text{δ 22}\text{.7 }\left({\text{CH}}_{\text{3}}\right)$

$\text{δ 32}\text{.0 }\left({\text{CH}}_{\text{2}}\right)$

$\text{δ 69}\text{.2 }\left(\text{CH}\right)$

$\text{δ 31}\text{.2 }\left({\text{CH}}_{\text{3}}\right)$

(three carbons)

$\text{δ 68}\text{.9 }\left(\text{C}\right)$

(one carbon)