1. General

The formal laboratory report is due on November 16, 2001 at 5 pm.

Review the following topics: distillation, IR, ¹H, ¹³C-NMR and Mass spectroscopy

Note for the teaching assistant: assign a different unknown to each of your student if possible

2. Experiment

Safety note: AlCl₃ and acetyl chloride are noxious and corrosive. Wear gloves when you handle them.

Anhydrous aluminum trichloride is a fine powder with a yellow-greenish tint. It is very hygroscopic. If the aluminum trichoride that you are using does not show these properties, consult your teaching assistant.

The color of yoru solution highly depends on which compound you are acylating and the concentration. Don't worry if you have the same unknown and observe a different color.

The steel wool in the neck of the Hickman head has to be trimmed.IIt is important that you have a good seal during the vacuum distillation. The steel wool prevents the crude product from bumping over during the distillation, but also works like a sponge. It needs to be heated with the heat gun to release the condensed product.

Obtain an IR, an ¹H-NMR, ¹³C-NMR and Mass spectrum for your final compound. An IR spectrum for your unknown starting material would help as well.

3. Things to think about

a. Student B uses AlCl₃*6H₂O as catalyst for his FC-acylation. The reaction failed. Why?

b. Student C has the task to synthesize 4-Diethylbenzene starting from benzene. How?

c. Student D attempts to perform a FC acylation with N-methylaniline. The reaction does not afford the desired product. Why?