CHM 266 Spring 2007 Organic Chemistry Lab

Experiment 6 Friedel-Crafts Acylation    (40 points)

A. Turn in your samples in a labeled bottle.  Include (4 pt., deductions will apply for lower yield, off boiling points and poor quality of product)

· Compound Name

· Your name

· Date

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

· Tare Weight of Bottle

· NFPA #'s

· Boiling 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)

F. Write the procedure in a journal style format for each step separately. Include the IR, ¹H and ¹³C NMR 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, and NMR in the procedure. The procedure will be worth 4 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.

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

· IR data missing in procedure -0.5 pt.

· ¹H NMR data missing in procedure -0.5 pt.

· ¹³ NMR 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. Assign all of the peaks in ¹H and ¹³ NMR spectra to protons and carbons of the product and calculate the coupling constant in doublets in ¹H NMR spectrum. Based on these two spectra and boiling point of the product decide which isomer of methylacetophenone is your product (8 pt.)

H. Answer questions 1 (2 pt.), 2 (1 pt.), 3 (2 pt.), 6 (1 pt.), 7 (1 pt.), and 8 (2 pt.) on page 536-7.

I. Based on the calculation results

· show the Mullikan charges at different carbons of the benzene rings in nitrobenzene, dimetheylaniline, phenol and phenoxide ion.

· Based on these results explain which carbon of the ring is more reactive in an electrophhilic aromatic substitution.

· Explain which one of these four compounds is the least reactive.

· Between Phenol and phenoxide ion which one is more reactive.

· Based on the calculation results, explain which one of the sigma-complexes of your assigned compound is more stable and how the three sigma-complexes will lead to the major product of nitration reaction of that compound. Energy of all calculated structures should be given and then relative energy must be calculated. (The structure with lowest energy will be assigned as zero and it’s energy must be subtracted from the energy of other two structures) (overall 10 points)

J. Staple IR spectrum, ¹H and ¹³C NMR of the product. (4 pt. with possible deductions for poor quality)