1. General

At this point in the quarter, it would be very advisable to review your IR and NMR notes from lecture. You are expected to have mastered these topics by the time the final exam comes around. You will need to memorize the most important numbers and trends for the exam since there will no tables provided!

Note for the teaching assistant: the students should start the reflux first and can take the test during this period of time

2. Experiment

Safety note: Concentrated sulfuric acid is very corrosive. Wear nitrile gloves when you transfer it! Avoid spills on your clothes since it will ruin them!

For this week’s experiment it is important that the glassware is dry. Why?

Be careful when you do the extractions with sodium bicarbonate in the conical vial or centrifuge tube. Mix the two layers with a spatula or a small glass rod (especially the first time!).

Make sure that the cap is on tight. Don't forget to vent frequently when you shake it.

Add only a small amount of drying reagent, otherwise significant amounts of the product will be lost.

If you only have a small amount of crude product, pre-weigh the Hickman head before the second distillation.

3. Things to think about

a. Why do you use an excess of acetic acid and not an excess of the alcohol in this experiment?

b. Do you expect the esterification to go to completion? How can you improve the yield of the ester using the same reagents?

c. Why are esters very important compounds in industry?

d. Why do you have to wrap a cold paper towel around the air condenser?

e. Why do you have to heat the mixture to a boil?