Question

Identify the compound with a molecular formula ${\mathbf{C}}_8{\mathbf{H}}_{10}\mathbf{O}$ that gives the IR and ${}^{\mathbf{1}}\mathbf{H}$NMR spectra shown here.

Short answer

The structure of the compound is as follows;

Step-by-step solution

Step-by-Step SolutionStep 1: Information given by IR spectra

IR spectroscopy is used for the identification of the functional groups in the given compound.

In the given compound, IR spectra peaks in the region 1500${\text{cm}}^{\text{-1}}$ and 1600${\text{cm}}^{\text{-1}}$ which indicate the presence of a benzene ring with hydrogen bonded to ${\text{sp}}^{\text{2}}$carbon atom. Also, the absorption band in 1250-1000${\text{cm}}^{\text{-1}}$ indicates the presence of role="math" localid="1652271799324" $\text{C-O}$bond.

Information given by the NMR spectra

The two singlets integrate into 3 protons suggesting the presence of two methyl groups. Also, the peak at 6.7-7.1 ppm indicates the presence of a benzene ring consisting of two doublets integrated with two hydrogens indicating the presence of 1, 4 di-substituted benzene ring.

The structure of the compound is as follows;

Given compound