Experiment Title

Name ________
Date ____2-21-14___________
Section ___3020-101_________

Equation (structural)

Stoichiometric Data (For any reactants that are part of the balanced equation, base
on the amounts measured in lab)
Compounds
Mole Wt.

Mass or volume

Moles

Reactants (actual)
Borneol

154.25 g/mol

0.193 g

*.00125 mol

Sodium
Hypochlorite (5%)

74.44 g/mol

2.0 g

*0.03 mol

Glacial acetic acid

60.05 g/mol

.15 g

*0.0025

Product
(theoretical)
camphor

152.23 g/mol

* .99 g

*.0065 mol

Product Data
Mass
.59 g

Percent Yield
*60%

bp or mp
Lit. 175-177C

Exptl.167-170 C

Spectroscopic Data (add or delete lines as necessary)

wavenumber
identity**
IR
Reactant
3600
Borneol
3000
C-H stretching

1700
3000

camphor

Product

C-H stretching

Product Structure (correlated to**)

By examination of the infrared peaks, you are able to determine if the
borneol (an alcohol OH stretch) is absent, or nearly absent, and if the
borneol has been oxidized to camphor (a ketone C=O stretch). This
means the oxidation was successful.

Discussion
The purpose of this experiment was to show to prepare a ketone via an oxidation
reaction of a secondary alocohol borneol and the methods of reaction, purifiying and
spectroscopic analysis. First, a water bath was prepared and put on a hot plate and a
micro reflux apparatus with a round bottom flask. About .5mL and .15 mL of of acetone
and acetic acid was added with a stir vane put over the water bath. Slowly, 2 mL of
NaOCl was added to the vial. The mixture was then tested with starch-KI test paper and
turned positive. The mixture was then cooled to room temp. and rinsed with
dichloromethane. This layer was then transferred into a clean centifuge tube. This set was
than repeated two more times. The dichloromethane was next washed with 1 mL of
sodium bicarbnate and the dichloromethane was transferred again to another centrufuge
tube. Next, it was washed with 1 mL of sodium bisulfite and 1 ml water. The
dichloromethane layer was then seperated out into a test tube and dried with sodium
sulfate. The solvent was then evaporated in the water bath and the test tube cooled until
the next lab period. The melting range was then determined to be 167-170C with an 60%
product yield. In summary, the active oxidizing agent in this experiment was
hyprochlorous acid. Sodium hypochlorite was converted to HOCl in an acid/base
reaction with acetic acid. Since oxygen has a higher electronegativity than chlorine, the
chlorine atom in HOCl has a slightly positive charge; as a result it acts as an electrophile.
The oxygen from borneols hydroxyl group acts a nucleophile and attacks the chlorine.
An OH- is released, that deprotonates the oxygen on borneol chloride to form an alkyl
hypochlorite. The alkyl hypochlorite was then deprotonated by water. A chloride ion was
thus released and a ketone was formed.

Appendix 1
Calculations
1) Show calculation for each starred (*) item in the report.
2) Include a stoichiometric equation if the structural one is not balanced.
.00648 mol product x 152.23 g/mol = .99 g of product
.99 g / 152.23 g/mol = .0065 mol product
1.25 mmole of OH = .00125 mol OH x 154.25 g/mol = 0.193 g OH
Actual .59 g/ theoretical .99 x 100 = 60% yield
2.0 g/74.44 g/mol= 0.0269 mol acetic acid
.15 g/ 60.05 g/mol = .0025 mol sodium hypochlorite
Oxidation-Reduction
Borneol (NaOCl, CH3COOH) - Camphor (NaSH4) - Isoborneol

Appendix 2
References
(Includes sources for physical constants and hazard information.)

Brown, H. C., and Muzzio, J. "Rates of Reaction of Sodium Borohydride

with Bicyclic Ketones." Journal of the American Chemical Society, 88(1966):
2811.
Dauben, W. G., Fonken, G. J., and Noyce, D. S. "Stereochemistry of
Hydride Reductions." Journal of the American Chemical Society, 78 (1956): 2579.