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The H1NMR spectra for two esters with molecular formula C8H8O2 are shown next. Which of the esters is hydrolyzed more rapidly in an aqueous solution with a pH of 10?

Short Answer

Expert verified

Following ester will hydrolyze more rapidly:

Step by step solution

01

Step-by-step-solutionStep 1: H1NMR spectroscopy

The chemical shift in H1NMR spectroscopy denoted as role="math" localid="1652430408976" δtells about the environment around the atomic nuclei. The δscale comprises a value in the range of 0-10 ppm. A high chemical shift value indicates the proton is deshielded and a low chemical shift value shows the proton is shielded.

02

Identifying the desired ester

Each of the NMR spectra possesses signals between 7 and 8 ppm (integrating to five hydrogens).This indicates that the compound has a benzene ring with one substituent.

There is an additional signal that is a singlet. The singlet in each spectrum is due to the methyl group. The methyl group is at a higher frequency on the second spectrum. This is the spectrum of the compound on the right, as the methyl group is near to an electron-withdrawing oxygen. The compound on the left is hydrolyzed more rapidly as its OR group is a weaker base. ( The pKaof phenol is approximately equal to 10 and that of methanol is approximately equal to 16).

Different esters

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