overhead projector edited by
demon/tration/
Change in Optical Rotation with Wavelength
E. Koubek and H. Quinn
U.S. Naval Academy
Annapolis, MD 21402
Recently in this column Hambly1 described a demonstra-
tion involving a solution of sucrose contained in a 50-mL
graduated cylinder. This is a simplified version of that dem-
onstration. It is easier to prepare and to carry out, and the
visual image is much larger. The demonstration can be used
to illustrate the effect of an optically active material on
plane-polarized light, as well as to show that the light rota-
tion is a function of the wavelength of the light used.
Procedure: Place a polarizing film2 on an overhead projec-
tor. Set a small crystallizing dish containing about 1 in. of
Karo light corn syrup on top of the film, and then place
See https://pubs.acs.org/sharingguidelines for options on how to legitimately share published articles.
another piece of polarizing film on top of the dish. By rotat-
Downloaded via UNIV DE ALICANTE on April 24, 2023 at 07:49:48 (UTC).
ing the top sheet of film, it can be shown that blue light is
transmitted first, and then other colors of the rainbow ap-
pear as the film is rotated through larger angles. Not only is
this a colorful demonstration, but it also explains why mono-
chromatic sodium D light is used in a polarimeter.
1
Hambly, G. F. J. Chem. Educ. 1988, 65, 623.
2
Available from Edmund Scientific Co., Barrington, NJ 08007.
Aromatic Pi Cloud Availability: Formation of
Colored Charge-Transfer Complexes
Kenneth E. Kolb
Bradley University
Peoria, IL 61625
In organic lectures the comparative availability of the pi
electron cloud of the benzene ring is correlated with the
reactivity of various substituted benzenes. One way to dem-
onstrate the variance of pi electron availability in the ben-
zene ring is to observe the color of the charge-transfer com-
plex formed between an aromatic compound and tetracyan-
oethylene (TCNE). The absorptivity and color of the
resulting complex correlates well, in a qualitative manner,
with the availability of pi electrons in the aromatic com-
pound and hence with its ease of electrophilic aromatic sub-
stitution. Thus benzene compounds containing meta-direct-
ing deactivating substituents, such as trifluoromethylben-
zene, form no pi complex with TCNE and give no color when
Doris Kolb
Bradley University
Peoria, IL 61625
mixed with TCNE. On the other hand, benzene derivatives
containing an increasing number of methyl groups form
TCNE charge-transfer complexes increasingly of greater
color in terms of depth and wavelength shift. The formation
of the colored complexes can be illustrated by adding a few
drops of colorless aromatic compound (e.g., methylbenzene)
to a few milliliters of a colorless solution of TCNE (1% in
CH2CI2) in a small beaker on the stage of an overhead projec-
tor. Immediately upon mixing, the solution turns bright
yellow-orange. With mesitylene, 1,3,5-trimethylbenzene,
the color produced is a much deeper orange-red. An easy
way to demonstrate these colored charge-transfer complex-
es, graphically illustrating the correlation of color and reac-
tivity, is to prepare a set of small French square bottles
containing various aromatic compounds plus TCNE and to
compare the colors. To prepare the samples add 2.0 mL of
TCNE solution (1% in CH2CI2) to a half-ounce French
square bottle; then fill the bottle with an aromatic com-
pound, and screw on the cap. (Caution: Samples should be
prepared in a well-ventilated hood, and gloves should be
worn when handling TCNE.) For solid aromatic compounds
(e.g., hexamethylbenzene) or for those compounds whose
absorption is too great to transmit light (e.g., methoxyben-
zene), CH2CI2 can be used to dilute the solution until it is
transparent. Prepared in this manner, the capped French
square bottles can be laid side by side on the stage of an
overhead projector to allow the whole class to see the array of
colors associated with the various aromatic compounds. The
mixtures are usually stable for several months. An interest-
ing informative display can be made by using some of the
following benzene derivatives:
_Aromatic Color of Complex
trifluoromethylbenzene none
benzonitrile none
benzene light yellow
methylbenzene yellow-orange
1,3-dimethylbenzene orange
1,3,5-trimethylbenzene orange-red
hexamethylbenzene (diluted) purple-violet
methoxybenzene (diluted) dark lavender
fluorobenzene lemon yellow
chlorobenzene yellow
bromobenzene darker yellow
iodobenzene red-orange
In the first group of compounds, which goes from deacti-
vated aromatic rings to very active ones, the color changes
progressively from colorless to deep lavender. In the second
group the colors show that with bromobenzene and iodoben-
zene the pi cloud is more available for complexation than
with fluorobenzene or chlorobenzene.
Volume 66 Number 10 October 1989 853