Question

When a compound with molecular formula ${\mathbf{C}}_{11}{\mathbf{H}}_{14}{\mathbf{O}}_2$undergoes acid-catalyzed hydrolysis, one of the products that is isolated gives the following ${}^1\mathbf{H}$NMR spectrum. Identify the compound.

Short answer

The given compound is isobutyl benzoate.

Step-by-step solution

Step-by-step-solutionStep 1: H1NMR spectroscopy

The${}^{\mathbf{1}}\mathbf{H}$NMR spectroscopy is used to understand the structure of various compounds. It helps in detecting the protons and the different types of protons in a compound can be identified using this technique.The different protons comprise different chemical shift values.

Compound produced when the molecular formula C11H14O2 undergoes acid-catalyzed hydrolysis

The spectrum shows that the compound contains four different hydrogens with a relative ratio of 2:1:1:6. The doublet at 0.9 ppm that integrates to six protons indicates that the compound has an isopropyl group. The signal at 3.4 ppm that integrates to two hydrogens indicates a methylene group connected to oxygen. It can be concluded that the given spectrum is of isobutyl alcohol. The molecular formula suggests that undergoes hydrolysis is an ester. Subtracting the atoms because of the isobutyl group let us identify the ester as isobutyl benzoate.

Acid catalyzed hydrolysis