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LEWIS DOT STRUCTURES

The steps below outline general guidelines for drawing the Lewis dot structures for covalent compounds and polyatomic
ions with a central atom. This theory of bonding will become a powerful tool for understanding how chemical
substances behave physically and chemically. Three representative examples are provided as reference.

1. Count Valence Electrons: Using the molecular formula, find the total number of valence electrons:
 Add up valence electrons for all atoms. We will most typically work with main groups elements, with valence
electrons in the outer most s & p orbitals.
 For each negative (-) charge, add one electron to the total.
 For each positive (+) charge, subtract one electron from the total.
HINT: For the vast majority of stable molecules or ions we encounter, the total number of valence electrons will be EVEN.
While molecules with odd numbers of electrons are found, they often are highly reactive radicals with unpaired electrons.

CH3CH2OH NO3- SO32-


1 Carbon: 2 x (4 valence electrons) 1 Nitrogen: 1 x (5 valence electrons) 1 Sulfur: 1 x (6 valence electrons)
6 Hydrogens: 6 x (1 valence electron) 3 Oxygens: 3 x (6 valence electrons) 3 Oxygens: 3 x (6 valence electrons)
1 Oxygens: 1 x (6 valence electrons) Monoanion: 1 extra electron Dianion: 2 extra electrons
Total: 8 + 6 + 6 = 20 electrons Total: 5 + 18 + 1 = 24 electrons Total: 6 + 18 + 2 = 26 electrons

2. Determine Connectivity: Decide how the atoms are connected


together. In some cases this will be given, as in CH3CH2OH. Here the formula
suggests the three hydrogens are associated with one carbon, which is
attached to another carbon with two bonded hydrogens, which is then
connected to an oxygen which has an associated hydrogen.

When the connections are not provided based on the formula, use the general rules below:
 Place the LEAST electronegative element in the center, surrounded
by the other atoms. With a weaker pull on electrons, the less
electronegative element can afford to share more electrons than
elements with higher electronegativities (which would be placed on
the outside of the molecule or ion).
 Hydrogen will never be in the center. It can only form a duet of
electrons maximum (1s2), and therefore can only form 1 bond with
another element.

3. Connect the central atoms to the outer atoms with single bonds.
Each single line represents the sharing of 2 electrons; without sharing electrons, the atoms will not be associated with
one another in a covalent molecule.

Each single line corresponds to a bond order of 1. All else being equal, the higher the bond order, the strong the
covalent bond and the short the bond length. A bond order to 2 would represent the sharing of 2 electron pairs (or 4
electrons total). A bond order of 3 would represent the sharing of 3 electron pairs (or 6 electrons total). Each of the
bonds above currently have a bond order of 1. Proceed to the next steps to learn how higher bond orders are possible in
Lewis dot structures.
4. Complete octets on outer atoms by adding lone pair electrons.
Remember single bonds represent 2 electrons, and an octet represents 8 electrons total around an atom. Hydrogen will
only have one bond to another atom to fulfill its duet (2 electrons maximum).

5. Adding any remaining valence electrons to the central atom as lone pair electrons.
Do this by comparing the total number of electrons in the structure at step 4 above, to the
total number of electrons needed, as calculated in step 1. In the first two examples
(CH3CH2OH) and NO3-, the total number of valence electrons has already been reached (20 &
24 electrons, respectively); no more electrons can be added to these structures.

In the case of sulfite (SO32-), only 24 electrons are accounted for at step 4. Two additional
electrons are needed to get to the total of 26 valence electrons; these are added as a lone
pair to the central sulfur atom (see structure at left).
At this point, all of the valence electrons should be accounted for. Do not add any additional electrons.

6. If needed, form double or triple bonds to complete the octet of the central atom.
Remember additional electrons cannot be added at this point.
Instead, pull lone pair electrons in from the outer atoms to form
the double or triple bonds. In the case of CH3CH2OH & SO32-, every
atom has a complete octet. In step 4 above, the central nitrogen of →
NO3- only has 6 electrons. To reach a complete octet, use one the
electron pairs on an outer oxygen to form an N=O double bond.
Notice the modified structure to the right still has 24 electrons, but
the nitrogen now has 8 total electrons around it.
Elements in groups 2A & 3A (columns with beryllium and boron) do not have large enough electronegativities to attain
an octet. These elements can have less than 8 electrons.

7. If necessary, minimize formal charge by changing lone pairs to bonds. See the table below
for a generalized approach to minimizing formal chage.
NOT MINIMIZED Improved, but not minimized Formal Charge MINIMIZED

To complete this step, first evaluate the formal charge for all atoms in the structure. To assign formal charge, find the
number of valence electrons for that element (from the periodic table). Then, subtract the number of electrons assigned
to the atom in the Lewis dot structure: 1 electron per bond and 2 electrons per lone pair. The equation for formal charge
(below) applies to one atom at a time, and involves only the electrons surrounding that particular atom.

𝑁𝑢𝑚𝑏𝑒𝑟 𝑜𝑓 𝑣𝑎𝑙𝑒𝑛𝑐𝑒 𝑒𝑙𝑒𝑐𝑡𝑟𝑜𝑛𝑠 𝑁𝑢𝑚𝑏𝑒𝑟 𝑜𝑓 𝑛𝑜𝑛𝑏𝑜𝑛𝑑𝑖𝑛𝑔 1


𝐹𝑜𝑟𝑚𝑎𝑙 𝐶ℎ𝑎𝑟𝑔𝑒 = ( )−( ) − (𝑁𝑢𝑚𝑏𝑒𝑟 𝑜𝑓 𝑒𝑙𝑒𝑐𝑡𝑟𝑜𝑛𝑠 𝑖𝑛 𝑏𝑜𝑛𝑑𝑠)
𝑖𝑛 𝑓𝑟𝑒𝑒 𝑛𝑒𝑢𝑡𝑟𝑎𝑙 𝑎𝑡𝑜𝑚 𝑒𝑙𝑒𝑐𝑡𝑟𝑜𝑛𝑠 𝑖𝑛 𝑙𝑜𝑛𝑒 𝑝𝑎𝑖𝑟𝑠 2
In the case of CH3CH2OH, the formal charge is already minimized;
all atoms have a formal charge of zero. In the case of NO3-, the
formal charge could not be minimized further without violating
the octet at nitrogen No additional modification is necessary to
these structures. These represents reasonable and valid Lewis
dot structures.

NEVER violate the octet on carbon, nitrogen, oxygen or fluorine, even if doing so would
minimize formal charge.
Formal Charge MINIMIZED In the case of SO32-, assigning formal charge yields the result
NOT MINIMIZED to the left. In the unminimized structure, the sulfur is electron
(Preferred Structure)
deficient (+1) and the oxygen atoms are electron rich (-1). This
structure can be improved by moving a lone pair of electrons
from an outer oxygen atom to form a double bond with
sulfur. Combining positive with negative lowers the energy of
the Lewis dot structure. In this way, the structure to the right
has formal charge minimized and better reflects the reality of
bonding in sulfite.
When the formal charge has been minimized as much as possible: any negative formal charge should be placed on the
more electronegative element; positive formal charge should reside on the less electronegative element.
Expanded Octets: In the case above, there are now more than 8 electrons around sulfur. Central atoms in the third row of
the periodic table or below (any element past neon) may have more than 8 electrons. This is called an expanded octet.
These atoms have opened up an energy level with d orbitals, but have no electrons in that d subshell. These d-orbitals are
available for bonding with other atoms.
Why minimize formal charge?
Formal charge is a way of tracking electron distribution within a proposed Lewis dot structure—a form of electron
bookkeeping. If the electrons were assumed to be distributed evenly within covalent bonds, the formal charge would
specify the charge on each individual atom. Where possible, formal charge should be 0. Minimizing formal charge
minimizes charge separation within the molecule, which produces lower energy structures. It takes energy to pull
positive away from negative, so a structure with formal charges of +1 and -1 on two atoms is higher in energy than a
structure with formal charges of 0 & 0.

8. Write resonance structures,


where possible.
In many cases, when a molecule has double or triple
bonds, these bonding electrons can be written in
different locations. These possibilities give rise to
unique Lewis dot structures (called resonance
structures) that collectively describe bonding in the
actual molecule. To accurately describe bonding in nitrate, for example, all three resonance structures (above) are
required. Each structure (equal in energy) contributes to the reality of the molecule, and no one structure in and of itself
would be adequate.
We say bonding in NO3- can be described as a weighted average of all three resonance structures. The result is a
resonance hybrid that shows lone pair electrons and double bond electrons spread out, or delocalized across all of the
atoms. While each individual structure shows localized N—O single bonds (bond order 1) and N=O double bonds (bond
order 2), the ion in reality has three equivalent nitrogen-oxygen bonds. Each individual bond in nitrogen is somewhat
mixed between a single bond and double bond with a bond order between 1 & 2. To calculate bond order, count the
total number of bonds share between the atoms (4 bonds), and divide by the total number of bonding regions (3).
Therefore, each bond in nitrate has a bond order of 4/3 or 1 1/3 (slightly closer to a single bond than a double bond).
𝑩𝒐𝒏𝒅 𝑶𝒓𝒅𝒆𝒓 = (𝑵𝒖𝒎𝒃𝒆𝒓 𝒐𝒇 𝒃𝒐𝒏𝒅𝒔 𝒔𝒉𝒂𝒓𝒆 𝒃𝒆𝒕𝒘𝒆𝒆𝒏 𝒂𝒕𝒐𝒎𝒔)/(𝑵𝒖𝒎𝒃𝒆𝒓 𝒐𝒇 𝒃𝒐𝒏𝒅𝒊𝒏𝒈 𝒓𝒆𝒈𝒊𝒐𝒏𝒔)

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