1. General

Make sure that you keep writing your formal report. See your teaching assistant or instructor if you have questions about the format.

Review the following topics: ¹H-NMR and ¹³C-NMR spectroscopy, GC/MS

2. Experiment

Safety note: Concentrated sulfuric and nitric acid are very corrosive. Wear nitrile gloves when you transfer them.

The ester has to be dissolved in concentrated sulfuric acid first before the acid mixture is added.

Make sure that you cool the mixture in an ice bath. Add the acid mixture dropwise. Why?

If you obtain an oil after you poured your reaction mixture on ice, add more ice and some water and keep mixing until the mixture solidifies.

Do not use too much methanol (even if it is cold) to wash your crude product. You will lose significant amounts!

3. Things to think about

a. Why do you have to control the temperature of the mixture very carefully?

b. What are methods to generate a nitronium ion?

c. The nitration of phenol usually leads to a polynitrated product even under much milder conditions. Why?

d. What do you expect to see in the ¹H-NMR spectrum and the ¹³C-NMR spectrum of the final product?