1. General

Review the following topics: extraction, recrystallization, organometallic chemistry

2. Experiment

a. Safety

1.  4-Iodophenol is corrosive and an irritant.

2. Methanol is toxic and flammable.

b. Experiment

It is important that the reaction mixture is properly refluxed because the reagents do not dissolve well in cold water.

The addition of the hydrochloric acid has to be done careful because the carbon dioxide is formed in large quantities.

The crude product is recrystallized from a methanol:water (~1:1).

The catalyst is removed by filtration and disposed in a separate container that is provided by lab support.

3. Things to think about

a. Why are aryl iodides more reactive in this reaction than aryl chlorides?

b. What is the rate-determining step in the reaction?

c. Why is palladium used in the reaction and not magnesium?