Chapter 14, Problem 14.53P

Propose a structure consistent with each set of spectral data:

a. ${\text{C}}_{\text{4}}{\text{H}}_{\text{8}}{\text{Br}}_{\text{2}}$: IR peak at $3000-2850{\text{cm}}^{-1}$; NMR ( $\text{ppm}$):

$1.87$ (singlet, $\text{6H}$)

$36.86$ (singlet, $\text{2H}$)

b. ${\text{C}}_{\text{3}}{\text{H}}_{\text{6}}{\text{Br}}_{\text{2}}$: IR peak at $3000-2850{\text{cm}}^{-1}$; NMR ( $\text{ppm}$):

$2.4$ (quintet)

$3.5$ (triplet)

c. ${\text{C}}_{\text{5}}{\text{H}}_{\text{10}}{\text{O}}_{\text{2}}$: IR peak at $1740{\text{cm}}^{-1}$; NMR ( $\text{ppm}$):

$1.15$ (triplet, $\text{3H}$)

$2.30$ (quartet, $\text{2H}$)

$1.25$ (triplet, $\text{3H}$)

$4.72$ (quartet, $\text{2H}$)

d. ${\text{C}}_{\text{6}}{\text{H}}_{\text{14}}\text{O}$: IR peak at $3600-3200{\text{cm}}^{-1}$; NMR ( $\text{ppm}$):

$0.8$ (triplet, $\text{6H}$)

$1.5$ (quartet, $\text{4H}$)

$1.0$ (singlet, $\text{3H}$)

$1.6$ (singlet, $\text{1H}$)

e. ${\text{C}}_{\text{6}}{\text{H}}_{\text{14}}\text{O}$: IR peak at $3000-2850{\text{cm}}^{-1}$; NMR ( $\text{ppm}$):

$1.10$ (doublet, relative area $=6$)

$3.60$ (septet, relative area $=1$)

f. ${\text{C}}_{\text{3}}{\text{H}}_{\text{6}}\text{O}$: IR peak at $1730{\text{cm}}^{-1}$; NMR ( $\text{ppm}$):

$1.11$ (triplet)

$2.46$ (multiplet)

$9.79$ (triplet)