Denisse Cuarteros

Laboratory 4B: Green Oxidation of Borneol to Camphor

Short response
1. In your own words explain oxidation (from an organic chemistry standpoint).
Oxidation is commonly coined as the loss of electrons. In an organic chemistry standpoint, it
can also be termed as the loss of hydrogens when undergoing a chemical reaction. One good
example is the oxidation of borneol to camphor. Since borneol is a secondary alcohol, the
(COH) alcohol group in borneol was replaced by (C=O) in camphor, making it lose the
alcohol group and turning it into a ketone group.
2. Why is TLC a useful analytical technique for measuring reaction progress? When
would it not be useful?
TLC is very useful because it analyzes the polarity of each compound stained and it helps in
separating non-volatile components of a mixture by analyzing the stains it made on the TLC
plate (via Rf values). On an experiment, if the stains are visible and resembles the main
products, it means that the reaction is complete. However, if the main products stains are
not starting to resemble the products, it means that the reaction is not nearly complete. TLC
would not be very useful if the stains made were very large and too concentrated because it
will travel up into the stationary phase with pieces of streaks. It wouldnt also be very helpful
in analyzing volatile components because it is hard to distinguish and they evaporate easily.
3. Sketch your TLC plate on the outline provided below, clearly labeling all lanes and
spots. Briefly summarize what is happening.









At ~2 cm, the presence of borneol is still visible until 3 min., then
it disappeared at 6 min. The presence of the crude camphor can
be seen on 6 min-12 min. with a very yellowish-orange spot
while the spot for camphor is somewhat lighter on the 15 min.
spot. However, the presence of camphor is almost invisible on
the TLC and at the 15 min. spot, it does not look as clear as the
camphor spot. This means that the reaction isnt complete.
2 cm
0 3 6 9 12 15
Denisse Cuarteros


4. From the list of the 12 Principles of Green Chemistry (see module 1), select two that
have been implemented by changing from the Cr(VI) oxidation procedure to this
Oxone

procedure. Explain your choices. (Use the back if you need additional space)

Cr(VI) is considered to be highly toxic and is a major environment hazard. However, by
using green chemistry, the reactants used were products of (1) designing safer chemicals
and the experiment performed had been an (2) inherently safer chemistry for accident
prevention. Since Cr(VI) is a major environment hazard, the process of implementing
green chemistry made the reaction safer for accident prevention. Also, since Cr(VI) is
also a major environmental hazard, designing safer chemicals helps eliminates threats to
the environment that may affect biological health.