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The Golden Rules of Organic Chemistry
Your goal should be to understand, not memorize organic chemistry.
The following 7
Golden Rules should be learned at the beginning of this semester. These simple ideas
explain a very large number of things about the way organic molecules interact. Thus,
understanding the 7 Golden Rules will allow you to develop an intuitive feel for organic
chemistry, and things will make sense! (Warning: this means you will start thinking like a
chemist, but, of course, no one needs to know if you don't want them to know.)
1. Atoms prefer filled valence shells.
This rule explains why atoms make bonds, and the
type of bonds created. A corollary is that centers of electron density (bonds and lone pairs
of electrons) repel each other so they stay as far apart as possible. This latter rule, the
basis for the so-called VSEPR model, explains 3-dimensional molecular structure.
2. The most important question in chemistry is
"Where are the electrons?"
answer is that electrons are generally in higher amounts around the more electronegative
atoms (e.g. F, Cl, O, N). 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
3. Nature hates unpaired electrons.
If a molecule must have an unpaired electron
radical), it is better to have the unpaired electron distributed over as many atoms
as possible through resonance, inductive effects, and hyperconjugation.
4. Nature hates localized charges.
If a molecule must have a charge, it is better to have
the charge distributed over as many atoms as possible through resonance, inductive
effects, and hyperconjugation. In addition, when given the choice, it is better to have
more negative charge on a more electronegative atom (e.g. O), and more positive charge
on a less electronegative atom (e.g. C).
5. Most reactions involve nucleophiles (molecules with a location of particularly high
electron density) attacking electrophiles (molecules with a location of particularly
low electron density).
When in doubt, transfer a proton!
Thus, simply understanding
where electrons are provides you with the best way of analyzing new molecules so that
you will be able to PREDICT how they will react.