General Announcement (Please read!)

1. It has come to my attention that some students are not clear about certain policies in this course. There is no such policy in this lab course which discourages students from asking questions. The reason why you are here is to learn. This should also result in questions from the the student's side, which are welcome by the teaching assistants and the instructor. However, it is expected that the student comes prepared to the lab section in order to be able to complete the experiment in a timely fashion. The majority of the questions regarding the experiment (theory and practical issues) can be answered during lecture and office hours. A question also should demonstrate the student's ability to analyze the problem and be as specific as possible in his/her inquiry.

2. In the future, please do not study outside my office (YH3077E). My colleagues in the office suite try to get some work done, and the noise outside is rather disturbing i.e. cell phones, etc

ATTN: answers to the below questions are due at the start of your lab period; these answers should be part of your pre-lab write-up.

1. Referring to the Aldol reaction carried out in the lab, answer the following questions. Show pertinent equations where appropriate.

a. The procedure asks to use absolute ethanol for the reaction. Explain.

b. The reaction mixture has to be brought to a gentle reflux before the ethanolic KOH solution is added. Explain.

c. The crude product is recrystallized from recrystallized from a mixture of toluene:ethanol (1:1). Rationalize this choice.

d. How much of the solvent does a student need to recrystallize 0.240 g of crude product?

e. Why is it important to allow the solution to cool down slowly during the recrystallization step?

2. A student isolates 2.50 g of a crude product Y that shows the following solubilities (in g/100 mL) in methanol, water and dichloromethane. The impurity to be removed is relatively polar.

Note: Quantities are given in g/100 mL of solvent.

a. Which solvent should the student use for recrystallization? Rationalize your choice.

b. Assuming the recrystallization is carried out correctly, how much of the pure product would be recovered?

3. While running the following reaction

a student acquires a TLC for his reaction mixture using a plate coated with silica and a mixture of dichloromethane and hexane (1:3) as eluent. He observes the following result

Note: Compound D is not UV-active. Lane 1 is compound A, lane 2 is compound B and lane 3 is the sample from the reaction mixture.

a. Determine the R_f-values for compound A and compound B.

b. What can be said about the progress of the reaction?

c. His neighbor decides to use a solvent mixture diethyl ether and hexane (3:2) as eluent instead. Which changes would he observe?

d. Why is it important to use capillary spotters to apply the sample to the plate?