CHML212
Exp. 19 Oxidation of 9-Fluorenol
IN-LAB ASSIGNMENT: (EACH STUDENT will record the following data in his/her laboratory notebook in a well organized
manner during lab period. Yellow carbon copies will be submitted for grading along with Post-Lab assignment.) …..max
score = 20 pts.
6. Data/Calculations
a.
b.
c.
d.
e.
f.
g.
h.
i.
j.
k.
Initial mass of 9-fluorenol used
TLC diagram (s) with all cm measurements
Initial mass of 150 mL beaker
Final mass of 150 mL beaker + product
Final product mass
Physical state and color of product
Theoretical yield calculation
Percent yield calculation
Atom economy calculation
Cost per synthesis and cost per gram calculations
All TLC Rf value calculations
7. In-lab Question (The following question should be answered in laboratory notebook.)
a.
Using the mechanism proposed in this experiment, draw the product, and a complete mechanism for its
formation, for the following reaction:
OH
HOCl
Cl
H3O+
+
O
H
H
?
CHML212
Exp. 19 Oxidation of 9-Fluorenol
POST-LAB ASSIGNMENT: (EACH LAB GROUP will submit one copy of a typewritten, paragraph style report addressing
all of the points listed below. Must be written using PAST TENSE, PASSIVE VOICE. ) …..max score = 50 pts.
8. Experimental (Write 1-2 paragraphs including all of the following. Do NOT present a bulleted outline.)




What type of reaction did you perform?
Describe the actual synthetic procedure. Include names of any reactants used and desired product, as well as
name of solvent and catalyst used (if any). Be sure to give actual volumes/masses of compounds used during the
synthesis (not just what the lab manual tells you to use).
Describe the purification technique used to isolate the desired product, including names and actual volume/mass
of any compounds used during purification.
Describe the analytical technique used to evaluate the product, including names and actual volume/mass of any
compounds used during sample prep, and any type of spectral analysis used.
9. Results (Complete, then copy/paste completed tables into your document.)
Table 19.1 Experimental results
Theoretical Yield (g)
Actual Yield (g)
Percent Yield
Melting Range (oC)
Product Appearance
Table 19.2 Green chemistry results
Table 19.3 Final TLC analysis
Atom Economy (%)
Cost per Synthesis ($)
Cost per Gram ($/g)
Compound
TLC Rf values
Standards
Sample
9-fluorenone
9-fluorenol
Table 19.4 IR analysis
Functional Group
O-H stretch
C-O stretch
C=O stretch
sp2 CH stretch
Base Values (cm-1)
3200–3400
1000–1200
1705–1725
3000–3100
9-fluorenol
9-fluorenone
10. Discussion (Write 1-2 pages addressing all of the following points.)



Based on the TLC results, were the reactants completely converted to the desired product? Explain this
conclusion by giving the identity and Rf values of all provided standards and any compounds detected in the
sample during TLC analysis.
How can IR spectroscopy be used to differentiate between the reactant and the product in this experiment? Give
the identity of one type of absorption and explain how it could be used to determine whether or not the
conversion took place. Include the typical frequency and the actual frequency for this type of bond in your
statement.
Include a short comment addressing what could be done differently to improve the experimental results, if
repeated.