Question

Question: What is the structure of a compound of molecular formula ${\mathit{C}}_{\mathbf{10}}{\mathit{H}}_{\mathbf{14}}{\mathit{O}}_{\mathbf{2}}$ that shows a strong IR absorption at 3150–2850 role="math" localid="1648710122642" $\mathit{c}{\mathit{m}}^{\mathbf{-}\mathbf{1}}$and gives the following 1 H NMR absorptions: 1.4 (triplet, 6 H), 4.0 (quartet, 4 H), and 6.8 (singlet, 4 H) ppm

Short answer

Answer

Structure of compound

Step-by-step solution

Significance of IR and NMR data

IR and NMR data can provide chemical information about the compound that can help in determining the structure of an organic molecule

The presence of a specific functional group, chemical environment of an atom can be deduced using IR and NMR spectra data.

Elucidating the structure of organic compound

Molecular formula: $C_{10}{H}_{14}{O}_2$

$$\begin{gathered} Degreeofunsaturation=\frac{2\times 10+2+0-14-0}{2} \\ =\frac{22-14}{2} \\ =4 \end{gathered}$$

Degree of unsaturation 4 suggests presence of benzene ring in the molecule.

IR absorption at $3150-2850c{m}^{-1}$is for $s{p}^2$C-H stretching and $s{p}^3$C-H stretching

NMR data suggests there are three sets of protons.

Therefore, based on the data, the structure can be:

1,4-diethoxybenzene