CHM 266 Spring 2007 Organic Chemistry Lab

Experiment 3 Synthesis and recrystallization of adipic acid   

A. Turn in your samples in a labeled bottle.  Include

· Compound Name

· Your name

· Date

· Weight of Product (original at the end of recrystallization)

· Tare Weight of Bottle

· NFPA #'s

· Melting Pt.

Please fill out the report in the following order

B. Your Name (-0.5 pt. if missing)

C. Date (-0.5 pt. if missing)

D. Experiment Title and Number (-0.5 pt. if missing)

E. Write the equation of reaction (-0.5 pt. if missing)

F. Write the procedure in a journal style format for each step separately. Include the IR data in the procedure. Use this link and see the experimental section as an example of how to write the procedure and how to incorporate the data including mp, IR, NMR and MS in the procedure. The procedure will be worth 8 pt. The following deductions will be applied

· No yield stated in procedure -0.5 pt.

· No % yield given procedure -0.5 pt.

· Incorrect yield calculation -0.5 pt.

· Mp. pt. not given in procedure -0.5 pt.

· IR data missing in procedure -0.5 pt.

· Any unclear or incorrect statements (-0.3 pt. each)

· Spelling errors particularly for compounds, techniques, apparatuses, and instruments (-0.2 pt. each)

· Overall report is not typewritten (-2 pt.).

G. (4 pt.) Answer the following question.

1- What impurities might you plausibly expect to be in the crude product?

2- What is the byproduct of this reaction?

3- Which one of the following compounds have catalytic role in oxidation of cyclohexane to adipic acid? Sodium tungstate Na₂WO₄, Aliquat 336, potassium bisulfate and hydrogen peroxide H₂O₂?

4- Based on the following reaction, calculate the atom economy for the reaction. (Refer to the notes in Procedures and Notes page)

H. (4 pt.) Staple IR spectrum, and identify (“assign”) the major peaks in the spectrum.