CHM 266 Spring 2007 Organic Chemistry Lab

Experiment 2 Multistep Synthesis   

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 for three steps (1.5 pt, -0.5 pt. for each reaction missing)

F. Write the procedure in a journal style format for each step separately. Include the IR and MS data (Only for the first two steps) 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, and MS (molecular ion and base peak) in the procedure. The procedure will be worth 12 pt. The following deductions will be applied

· No yield stated in procedure -0.5 pt each.

· No % yield given procedure -0.5 pt each.

· Incorrect yield calculation -0.5 pt each.

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

· IR data missing in procedure -0.5 pt each.

· MS data (for the first two steps) missing in procedure (-0.5 pt each)

· 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. Report overall yield of the multistep synthesis. (1.5 pt)

H. separate table for IR spectrum of benzaldehyde (page 294) and three products that identifies the C-H, O-H, and C=O stretching and out of plane (oop) bending vibration of aromatic C-H. (5 pt.)

I. In the mass spectrum of benzoin and benzil which peaks are correspond to molecular ions and fragments shown below. (4 pt.)

J. Answer the following question.

1. (2 pt.) In oxidation of benzoin to benzil with nitric acid, why it is important to avoid heating the mixture above 70 °C. What is the possible side product if this happens.

2. (6 pt.) Answer question 4 on p. 294 and 1 on page 302 of the lab manual.

K. Staple IR spectra of all three samples, chromatogram and mass spectra of benzoin and benzil and MS of benzoin and benzil to end of report. Show the fragmentations on the mass spectra of benzoin and benzil. (8 pt. with possible deductions for poor quality).