This quarter, the students will perform Extra Credit Project (Synthesis of 4-(4-Chlorophenyl)-3,4-dihydropyrimidin-2-one). The prelab questions below refer to this project: The pre-lab questions (due together with the rest of the prelab by Friday, October 23, 2015 at 12:00 pm in the instructor's office) :

1. Why can this reaction be considered an example for "Green Chemistry"?

2. What is the function of p-toluenesulfonic acid in the reaction? Show the ke intermediate.

3. Why is it important to mix the solids thoroughly before storing the mixture?

4. What is used as solvent for the recrystallization? Rationalize this choice.

5. Why is the central six-membered ring almost planar?

6. How many signals are observed in the ¹³C-NMR spectrum of the compound? Where are they located?

Notes:

1. Please note that the student will use 4-chlorobenzaldehyde (1.40 g instead of 1.06 g of benzaldehyde) for the reaction this quarter. The procedure using benzaldehyde is outlined in the reader (Extra credit project II).

2. As part of the prelab the student has to include a proper infrared spectrum for the exact compound and mass spectrum, which has pertinent peaks labeled.

3. The experiment will be started on October 28, October 29 and November 3 and finished on November 4, November 5 and November 10 during which GC/MS samples can only be submitted.

4. The formal report will be due by Friday, November 20, 2015 at 12:00 pm in YH 3077E as hardcopy and by 1:00 pm on the same day on turnitin.com (Course ID: 10294604, Password: Chem30BL).  Note that like always, late paper or online submissions will not be accepted.