Procedure for Drawing Organic Lewis Structures

Dr. David Konas

1. Which atoms are present, and how many valence electrons are available to work with? You
must add electrons for molecular anions and subtract electrons for molecular cations.
2. Propose a connectivity for the molecule, and add bonding and non-bonding electron pairs as
necessary. You initial goal is to create a structure where all atoms have a filled valence
electron shell (called closed-shell). This will not always be possible for every atom in
every structure, but it should be a priority. Another priority will be configuring atoms to have
zero formal charge, unless you are dealing with a known molecular ion.
NOTES:
A. Closed-shell means 8 electrons for most atoms you will encounter in organic chemistry, and
2 electrons for hydrogen (H).
B. Some atoms (such as sulfur, S, in H2SO4) can be drawn with an expanded octet. However,
more than 8 electrons around the common atoms C, N, and O will never be correct.
C. Some atoms in the third column of the periodic table such as boron (B) and aluminum (Al) are
frequently seen with only 6 electrons around them and are therefore known as open shell.
The reason for this will become clear once you understand the concept of formal charge.
D. Sometimes the way the formula is presented will give you information on connectivity, and
sometimes it will not. For example: C4H10 vs. CH3CH2CH2CH3.

3. If you run out of electrons available before completing your structure, you probably need to
consider using multiple (double, triple) bonds (ie. sharing more that one pair of electrons)
between some atoms.
4. Simplify and clean up your structure by replacing pairs of bonding electrons with lines to
indicate covalent bonds. Nonbonding electrons (or lone pairs) are indicated with dots.
5. Calculate and add formal charges to individual atoms as needed. Every atom is considered
independently for the calculation of formal charge!
Formal Charge = # of Valence Electrons for the atom being considered in its
neutral form.
- 1 for each non-bonding electron around that atom.
- 1 for each bond to that atom.
The total (or net) charge on any molecule is the sum of all the formal charges on all atoms in
the molecule. All uncharged (or neutral) molecules have a net charge of zero.

6. Consider any other possible resonance structures for this compound. When you have multiple
resonance structures possible, evaluate which ones are good.
A good resonance structure is one that has as many atoms as possible with a closed shell,
and a minimal amount and separation of formal charges.

Once you have some practice following steps 1-5 above and become familiar
with the idea of formal charges, you will notice certain patterns! If you
combine that with the concept that the best structures you can draw have
the least amount of formal charge possible, then structure drawing becomes
much faster and simpler!!!
For example, in the case of a carbon (C), the atom will have zero formal charge and a filled
valence electron shell with four covalent bonds. Therefore, the goal when drawing structures will
simply be for all neutral carbon atoms to have four covalent bonds (and no non-bonding
electrons)!
Sometimes you will encounter carbon atoms which DO have a formal charge. These charges
will typically be +1 (cation) or -1 (anion). Based on the number of valence electrons for carbon
(4) and the formal charge formula, these carbon atoms will always have the following
arrangement of electrons:
Carbon with a -1 formal charge: 3 covalent bonds and one lone pair
Carbon with a +1 formal charge: 3 covalent bonds and no lone pair (It is open shell!).
Convince yourself this is true, and then learn the same trends for O, N, H, and halogens!
Once you know these patterns, draw your structures using them as guides rather than
counting up electrons and arranging atoms in more random fashion!!