Formal Charges

Not all atoms within a neutral molecule need be neutral

The location of any charges is often important for understanding reactivity.

Get into the habit of labelling the formal charges on any atoms.

The formal charge on an atom can be calculated using an equation or by instinct (!)

Check out some questions ?

Knowing the formal charge on a particular atom in a structure is an important part of keeping track of the electrons and
is important for establishing and predicting the reactivity.
Although formal charge can be calculated via a formula, see below, it is also possible to do it "instinctively" based on
comparing structures. The "instinctive method" is quicker, and is probably what your instructor uses, but it does require
more skill and an experience of common structures.
Formal charge equation is based on the comparing the number of electrons in the individual atom with that in the
structure:

Instinctive method
This is based on comparing the structure with common, known neutral structures. To do this you need to recognise the
common neutral structures: C 4 bonds, N 3 bonds, 1 lone pair, O 2 bonds, 2 lone pairs, F 1 bond, 3 lone pairs. Once
mastered, this is much quicker.
In the middle of the following diagram are the neutral bonding situations for C, N, O and a halogen, F. (Just think of
each central atom bond being to a hydrogen).
To the left, a bond has been lost but converted to a lone pair, so the central atom has gained an electron and become
-ve.
To the right, there are 2 scenarios:

C and F have lost the shared electrons of a bond, so losing one electron from the "count" to
become +ve.

N and O have converted two unshared electrons into a shared pair of electrons in a bond, so
losing one electron from the "count" to become +ve.

Introduction:
Sometimes atoms will have extra or not enough electron electrons. This imbalance of electrons is denoted with a
formal charge. A negative formal charge means there are too many electrons on atom. (Remember electrons are
negatively charged.) A positive formal charge means there are not enough electrons on an atom. One confusing
thing about formal charges is that we do not simply count up all of the electrons around an atom. Different types of
electrons are counted differently. Non-bonding electrons are counted individually. However, electrons in bonds are
counted as being shared and so each pair of electrons in a bond counts as only one electron.
How to:
To calculate formal charge of an atom, use the equation below. Take the valence number of the atom and subtract
the number of bonds and the number of non-bonding electrons.
Comments:
Counting electrons to calculate formal charges is different from counting electrons for octets. Shared electrons (in
bonds) and unshared electrons (in lone pairs) are counted differently.
Hint: Instead of calculating the formal charge for every atom in a molecule, it is a lot faster to identify the atoms
that deviate from the "typical" bonding patterns. The typical bonding patterns will be neutral (formal charge = 0).
So atoms that deviate from these will usually have a formal charge.
Formal Charge = (valence number) - (number of bonds) - (non-bonding e's)\

Examples:

Practice problems:

Answers:
(1a) Formal charge of the atom is?
+1
0
-1
No Answer
1b) Formal charge of the atom is?
+1
0
-1
No Answer
(1c) Formal charge of the atom is?
+1
0
-1
No Answer
(2a) Formal charge of the atom is?
+1
0
-1
No Answer
(2b) Formal charge of the atom is?
+1
0
-1
No Answer
(2c) Formal charge of the atom is?
+1
0
-1
No Answer
(3a) Formal charge of the atom is?
+1
0
-1
No Answer
(3b) Formal charge of the atom is?
+1
0
-1
No Answer
(3c) Formal charge of the atom is?
+1
0
-1
No Answer

Resonance structures are all the possible Lewis structures for a molecule. Formal charge is a technique to identify
which resonance structure is the more correct structure. The most correct Lewis structure will be the structure where the
formal charges are evenly distributed throughout the molecule. The sum of all the formal charges should equal the total
charge of the molecule.
Formal charge is the difference between the number of valence electrons of each atom and the number of electrons the
atom is associated with.
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The equation takes the form:
FC = eV - eN - eB/2
where
eV = number of valence electrons of the atom as if it were isolated from the molecule
eN = number of unbound valence electrons on the atom in the molecule
eB = number of electrons shared by the bonds to other atoms in the molecule
The two resonance structures in the above picture are for carbon dioxide, CO2. To determine which diagram is the
correct one, the formal charges for each atom must be calculated.
For Structure A:

eV for oxygen = 6
eV for carbon = 4
To find eN, count the number of electron dots around the atom.
eN for O1 = 4
eN for C = 0
eN for O2 = 4
To find eB, count the bonds to the atom. Each bond is formed by two electrons, one donated from each atom involved in
the bond. Multiply each bond by two to get the total number of electrons.
eB for O1 = 2 bonds = 4 electrons
eB for C = 4 bonds = 8 electrons
eB for O2 = 2 bonds = 4 electrons
Use these three values to calculate the formal charge on each atom.
Formal charge of O1 = eV - eN - eB/2
Formal charge of O1 = 6 - 4 - 4/2
Formal charge of O1 = 6 - 4 - 2
Formal charge of O1 = 0
Formal charge of C = eV - eN - eB/2
Formal charge of C1 = 4 - 0 - 4/2
Formal charge of O1 = 4 - 0 - 2
Formal charge of O1 = 0
Formal charge of O2 = eV - eN - eB/2
Formal charge of O2 = 6 - 4 - 4/2
Formal charge of O2 = 6 - 4 - 2
Formal charge of O2 = 0
For Structure B:
eN for O1 = 2
eN for C = 0
eN for O2 = 6
Formal charge of O1 = eV - eN - eB/2
Formal charge of O1 = 6 - 2 - 6/2
Formal charge of O1 = 6 - 2 - 3
Formal charge of O1 = +1
Formal charge of C = eV - eN - eB/2
Formal charge of C1 = 4 - 0 - 4/2
Formal charge of O1 = 4 - 0 - 2
Formal charge of O1 = 0
Formal charge of O2 = eV - eN - eB/2
Formal charge of O2 = 6 - 6 - 2/2

Formal charge of O2 = 6 - 6 - 1
Formal charge of O2 = -1
All the formal charges on Structure A equal zero, where the formal charges on Structure B show one end is positively
charged and the other is negatively charged.
Since the overall distribution of Structure A is zero, Structure A is the most correct Lewis structure for CO2.

Formal charge = [# of valence electrons] [electrons in lone pairs + 1/2 the number of bonding electrons]
This formula explicitly spells out the relationship between the number of bonding electrons and their relationship to how
many are formally owned by the atom. However, since the number of bonding electrons divided by 2 term is also
equal to the number of bonds surrounding the atom,heres the shortcut formula:
Formal Charge = [# of valence electrons on atom] [non-bonded electrons + number of bonds].
Lets apply it to some examples. for example BH4 (top left corner).

The number of valence electrons for boron is 3.

The number of non-bonded electrons is zero.
The number of bonds around boron is 4.

So formal charge = 3 (0 + 4) = 3 4 = 1
The formal charge of B in BH4 is negative 1.
Lets apply it to :CH3 (one to the right from BH4)

The number of valence electrons for carbon is 4

The number of non-bonded electrons is two (it has a lone pair)

The number of bonds around carbon is 3.

So formal charge = 4 (2 +3) = 4 5 = 1
The formal charge of C in :CH3 is negative 1.
Same formal charge as BH4!
Lets do one last example. Lets do CH3 (with no lone pairs on carbon). Its the orange one on the bottom row.

The number of valence electrons for carbon is 4

The number of non-bonded electrons is zero
The number of bonds around carbon is 3.

So formal charge = 4 (0 +3) = 4 3 = +1

You can apply this formula to any atom you care to name.
Here is a chart for some simple molecules along the series B C N O . I hope beryllium and fluorine arent too offended
that I skipped them, but theyre really not that interesting for the purposes of this table.

Note the interesting pattern in the geometries (highlighted in colour): BH4(), CH4, and NH4(+) all have the same
geometries, as do CH3(), NH3, and OH3(+). Carbocation CH3(+) has the same electronic configuration (and
geometry) as neutral borane, BH3. The familiar bent structure of water, H2O, is shared by the amide anion, NH2().
These shared geometries are one of the interesting consequences of valence shell electron pair repulsion theory
(VSEPR pronounced vesper, just like Favre is pronounced Farve.)
The formal charge formula also works for double and triple bonds:

Heres a question. Alkanes, alkenes, and alkynes are neutral, since there are four bonds and no unbonded electrons: 4
[4+0] = 0. For what other values of [bonds + nonbonded electrons] will you also get a value of zero, and what might
these structures look like? (Youll meet some of these structures later in the course).
One final question why do you think this is called formal charge?
Think about what the formal charge of BF4 would be. Negative charge on the boron. Whats the most electronegative
element here? Fluoride, of course, with an electronegativity of 4.0, with boron clocking in at 2.0. Where do you think
that negative charge really resides?
Well, it aint on boron. Its actually spread out through the more electronegative fluoride ions, which become more
electron-rich. So although the formal address of the negative charge is on boron, the electron density is actually
spread out over the fluorides. In other words, in this case the formal charge bears no resemblance to reality.

Cellular Respiration
We all need energy to function and we get this energy from the foods we eat. The most efficient way forcells to harvest
energy stored in food is through cellular respiration, a catabolic pathway for the production ofadenosine
triphosphate(ATP). ATP, a high energy molecule, is expended by working cells. Cellular respiration occurs in
botheukaryotic and prokaryotic cells. There are three main stages of cellular respiration: glycolysis, the citric acid cycle,
and electron transport/oxidative phosphorylation.

Glycolysis
Glycolysis literally means "splitting sugars." Glucose, a six carbon sugar, is split into twomolecules of a three carbon
sugar. Glycolysis takes place in the cell's cytoplasm. In the process, two molecules of ATP, two molecules of pyruvic

acid and two "high energy" electron carrying molecules of NADH are produced. Glycolysis can occur with or without
oxygen. In the presence of oxygen, glycolysis is the first stage of cellular respiration. Without oxygen, glycolysis allows
cells to make small amounts of ATP. This process is called fermentation.
Parts of Plant Cell
Plants cell constitute of membrane bound nucleus and many cellular structures. These organelles carry out functions
that are necessary for the proper functioning and survival of the cell. The cell organelles of the plant are enclosed by a
cell wall and cell membrane. The constituents of the cell are suspended in the cytoplasm or cytosol.
The parts of the plant cell are as follows:
Cell wall is the outermost rigid covering of the plant cell. It is a salient feature of plant cell.
Cell membrane or the plasma membrane is the outer lining of the cell inside the cell wall.
Cytosol or cytoplasm is the gel-like matrix inside the cell membrane which constitutes all other cell organelles.
Nucleus is the control center of the cell. It is a membrane bound structure which contains the hereditary material of the
cell - the DNA
Chloroplast is a plastid with green pigment chlorophyll. It traps light energy and converts it to chemical energy by the
process of photosynthesis.
Mitochondria carries out cellular respiration and provides energy to the cells.
Vacuoles are the temporary storage center of the cell.
Golgi body is the unit where proteins are sorted and packed.
Ribosomes are structures that assemble proteins.
Endoplasmic reticulum are membrane covered organelles that transport materials.