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The most
important question in chemistry is "Where are the electrons?"
The answer is that electrons are generally
in higher amounts around the more electronegative atoms (e.g. F,
Cl, O, N) of a molecule. The electronegative atoms pull electron density away
from the less electronegative atoms (e.g. C, H) to which they are bonded.
Thus, understanding electronegativities provides a simple method of deciding
which portions of a molecule have a relatively high electron density, and
which portions have a relatively low electron density. Molecules with areas
of high and low electron density are referred to as ‘polar’ molecules.
Molecules that have relatively uniform electron densities are referred to
as ‘nonpolar’ molecules.
Electronegativities of the atoms we will normally
encounter in organic chemistry:
H = 2.1, C = 2.5, S = 2.5, Br = 2.8, N = 3.0,
Cl = 3.0, O = 3.5, F = 4.0
Physical properties such as melting
points, boiling points and solubilities can be understood by analyzing distributions
of electron density. All things being equal, molecules that are more polar
will ‘stick’ to each other better, increasing both the melting points
and boiling points (it takes more energy and thus heat to break apart the
interactions between ‘sticky’ molecules). This is because unequal
distributions of electrons in a polar molecule produce corresponding partial
charges (remember that electrons are negatively charged), and opposite partial
charges attract each other, making the molecules stick together. Nonpolar
molecules do not have these partial charges, so they do not stick to each
other as well. Also, polar molecules dissolve in polar solvents, again because
of the attractions between partial charges on the solvent and the polar molecules.
Nonpolar molecules dissolve in nonpolar solvents.
Relative acidities are also understood
on the basis of electron distribution. When a molecule loses a proton, it
is acting as an Bronsted acid. Because a proton has a positive charge, losing
a proton generally leaves a negative charge behind. A molecule will be more
willing to give up a proton (i.e. it will be a stronger acid) the better
the negative charge can be absorbed after the proton leaves. A molecule can
better absorb a negative charge if it has more electronegative atoms that
can accommodate the negative charge. Later you will see how important it is
to be able to predict relative acidities of molecules in order to predict
important attributes such as relative ‘leaving group’ abilities.
Finally, and most importantly, understanding
where the electrons are located in a molecule allows for the understanding/prediction
of reactions. As you will learn, the vast majority of reactions involve
the electron rich portions of one molecule or species (the so-called ‘nucleophile’)
reacting with the extremely electron deficient portion of another molecule
(the so-called ‘electrophile’). Being able to understand and predict
reactions, then, comes down to being able to predict the locations of these
reactive sites (i.e. where are the electrons?).
The bottom line. Understanding where
electrons are in molecules (i.e. around the more electronegative atoms)
allows you to understand/predict physical properties, acidities and reactions
of molecules. It is just that simple. In short, you will understand organic
chemistry, it will make sense to you, it will be far easier than trying to
memorize a bunch of facts and your organic chemistry classes will be enjoyable.
O.K., maybe the word ‘enjoyable’ was a stretch here, but it will
be less painful than you are expecting. I guarantee |
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