1. General

Start your literature search for the formal report! Read and understand the guidelines for the formal report. The final version of the formal report will probably be due on November 27, 2002. Make sure that you start to do some reading about the chemistry that you perform in the laboratory while you doing the in-lab work.

2. Experiment

This week you should work up the reaction from step 2 (alcohol synthesis) and also perform the oxidation reaction (step 3b).

a. Work-up of Step 2 (Alcohol)

Pour the reaction mixture slowly into the water while stirring. It is also advisable to add the 36% HCl slowly to this mixture (Test the pH value with pH paper). This way the formed precipitate will not incorporate so much of the brown byproducts. Keep in mind that you perform a neutralization reaction.

After extraction and drying you should have a yellow solution. The solvent has to be boiled off in the hood leaving behind a viscous oil that crystallizes upon cooling (off white solid).

It is important to test the purity of the obtained alcohol by TLC. If the reaction didn't work well, there will be significant amount of the unreacted phenol present, which causes problems in the purification of the aldehyde.

b. Step 3 b (Oxidation of the alcohol with Ce(OH)₃(OOH))

It is important to keep the temperature of the reaction mixture between 50-70 C. Too low of a temperature slows down the reaction too much. A significantly higher temperature causes the Ce(OH)₃(OOH) to decompose without oxidizing the alcohol. Make sure that you collect the solid product (Ce(OH)₃) in a separate container for recycling.

You should perform the actual oxidation reaction this week, maybe even filter off the Ce(OH)₃ and do the rest of work-up next week.