Solved NMR Problems: Webspectra Beginner Problem #2

This is a continuation of my Solved NMR Problem series, where I solve NMR problems from various databases around the web. See this article for my basic method. In today’s article I’m going to solve Webspectra Beginner Problem #2.

(credit: Webspectra Beginner Problem #2)

Try it yourself before proceeding through the rest of this article. Make sure to click the above link to see the spectra in more detail!

Anyway:

1. C8H8O2

Degrees of Unsaturation = (18 – 8)/2 = 5

Already I’m suspecting an aromatic ring (which has a DoU of 4).

2. Pieces:

Again, the difficulty with Webspectra is that there are no integration ratios; you have to estimate them based on the heights of the red lines on the spectra (go to the site to see a more zoomed in version of the spectra so you can see the splitting patterns).

Here are my estimates:

3.8 ppm (singlet, 3H) Must…