Beruflich Dokumente
Kultur Dokumente
edited by
Ed Vitz
Kutztown University
Kutztown, PA 19530
Introducing chemical concepts to students by using concrete examples and interest-arousing demonstrations is a wellaccepted pedagogy. Demonstrations and activities pertaining
to invisible inks are popular (1). Natural indicators obtained
from common fruits, vegetables, teas, and flowers have been used
in a number of instructor demonstrations and simple student
experiments (2-9). These activities are engaging and attract
students' attention (1-9). We have developed a demonstration
utilizing invisible inks and solutions of three naturally occurring
dyes as developing agents. The demonstration not only attracts
students' attention but also illustrates the concepts of relative
acidities of alcohols, resonance stabilization, and keto-enol
tautomerization.
A core concept in undergraduate organic chemistry is that
the acidity of a functional group increases if the anion formed
(from loss of H) is stabilized. Both resonance and inductive
effects are considered when evaluating the relative acidities of
different molecules. However, many students rely more on recall
of memorized facts rather than on deductive reasoning when
predicting relative acidities. This may be because many students
have difficulties writing resonance structures. These students
may feel that they can arrive at a correct answer to predict
relative acidities (or relative reactivities) without drawing resonance structures. The demonstration can be used to introduce
exercises that provide students with additional practice drawing
resonance structures and predicting relative acidities.
The demonstration uses dilute basic solutions as invisible
inks. The inks are made visible using naturally occurring dyes
that undergo pH-dependent structural and color changes.
One of the developing agents is an ethanolic solution of the
2-hydroxy-1,4-naphthoquinone, which gives henna, a natural dye
used in hair colorants and in body decorations, its characteristic
color. Resonance theory predicts that 2-hydroxy-1,4-naphthoquinone should lose the hydrogen atom of its vinyl alcohol under
mild basic conditions as the corresponding anion formed is
resonance stabilized (Scheme 1). Delocalization of the electrons
(of the anion) results in a shift of the wavelengths absorbed by the
compound and a resultant change in color. A solution of
2-hydroxy-1,4-naphthoquinone is yellow under acidic conditions
but changes to reddish orange under basic conditions. A message
written on a filter paper with a basic solution such as dilute
Na2CO3 or NaOH becomes invisible on evaporation of the
solvent. When a solution of 2-hydroxy-1,4-naphthoquinone is
sprayed onto the filter paper, the deposited base reacts with the
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In the Classroom
pubs.acs.org/jchemeduc
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In the Classroom
pubs.acs.org/jchemeduc
In the Classroom
pubs.acs.org/jchemeduc
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