Chapter 22, Problem 22.81P

Identify the structures of each compound from the given data.

a. Molecular formula ${\text{C}}_{\text{6}}{\text{H}}_{\text{12}}{\text{O}}_{\text{2}}$

IR absorption: $1738{\text{cm}}^{-1}$

${}^{\text{1}}\text{H}$ NMR: $1.12$ (triplet, $\text{3}\text{H}$), $1.23$ (doublet, $\text{6}\text{H}$), $2.28$

(quartet, $\text{2}\text{H}$), and $5.00$ (septet, $\text{1}\text{H}$) ppm

b. Molecular formula ${\text{C}}_{\text{4}}{\text{H}}_{\text{7}}\text{N}$

IR absorption: $2250{\text{cm}}^{-1}$

${}^{\text{1}}\text{H}$ NMR: $1.08$ (triplet, $\text{3}\text{H}$), $1.70$ (multiplet, $\text{2}\text{H}$) and $2.34$

(triplet, $\text{2}\text{H}$) ppm

c. Molecular formula ${\text{C}}_{\text{8}}{\text{H}}_{\text{9}}\text{NO}$

IR absorption: $3328{\text{cm}}^{-1}$ and $1639{\text{cm}}^{-1}$

${}^{\text{1}}\text{H}$ NMR: $2.95$ (singlet, $\text{3}\text{H}$), $6.95$ (singlet, $\text{1}\text{H}$) and

$7.3-7.7$ (multiplet, $\text{5}\text{H}$) ppm

d. Molecular formula ${\text{C}}_{\text{4}}{\text{H}}_{\text{7}}\text{ClO}$

IR absorption: $1802{\text{cm}}^{-1}$

${}^{\text{1}}\text{H}$ NMR: $0.95$ (triplet, $\text{3}\text{H}$), $1.07$ (multiplet, $\text{2}\text{H}$) and $2.90$

(triplet, $\text{2}\text{H}$) ppm

e. Molecular formula ${\text{C}}_{\text{10}}{\text{H}}_{\text{12}}{\text{O}}_2$

IR absorption: $1740{\text{cm}}^{-1}$

${}^{\text{1}}\text{H}$ NMR: $1.2$ (triplet, $\text{3}\text{H}$), $2.4$ (quartet, $\text{2}\text{H}$), $5.1$ (singlet,

$\text{2}\text{H}$), and $7.1-7.5$ (multiplet, $\text{5}\text{H}$) ppm