Chapter 17, Problem 44P

Given here are the ${}^{1}H$ NMR spectra and carbonyl IR absorption peaks of five acyl compounds. Propose a structure for each.

(a) $C_8{H}_{12}{O}_4$ ${}^{1}H$ NMR SpectrumIR Spectrum

Triplet $\delta 1.2\left(6H\right)$ $1740c{m}^{-1}$

Singlet $\delta 2.5\left(4H\right)$

Quartet $\delta 4.1\left(4H\right)$

(b) $C_{11}{H}_{14}{O}_2$ ${}^{1}H$ NMR SpectrumIR Spectrum

Doublet $\delta 1.0\left(6H\right)$ $1720c{m}^{-1}$

Multiplet $\delta 2.1\left(1H\right)$

Doublet $\delta 4.1\left(2H\right)$

Multiplet $\delta 7.8\left(5H\right)$

(c) $C_{10}{H}_{12}{O}_2$ ${}^{1}H$ NMR SpectrumIR Spectrum

Triplet $\delta 1.2\left(3H\right)$ $1740c{m}^{-1}$

Singlet $\delta 3.5\left(2H\right)$

Quartet $\delta 4.1\left(2H\right)$

Multiplet $\delta 7.3\left(5H\right)$

(d) $C_2{H}_{2}C{l}_2{O}_2$ ${}^{1}H$ NMR SpectrumIR Spectrum

Singlet $\delta 6.0$ Borad peak 2500–2700 $c{m}^{-1}$

Singlet $\delta 11.70$ $1705c{m}^{-1}$

(e) $C_4{H}_{7}Cl{O}_2$ ${}^{1}H$ NMR SpectrumIR Spectrum

Triplet $\delta 1.3$ $1745c{m}^{-1}$

Singlet $\delta 4.0$

Quartet $\delta 4.2$