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Calculating Formal Charges: Determining Atom Charges in Chemistry, Schemes and Mind Maps of Organic Chemistry

An introduction to the concept of formal charges in chemistry, explaining what formal charges are, how they are calculated, and their significance in understanding electron density and flow in molecules. examples of calculating formal charges for various atoms in different molecules, such as nitrogen, oxygen, and carbon.

Typology: Schemes and Mind Maps

2021/2022

Uploaded on 09/12/2022

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Calculating Formal
Charges
Simple but significant
What is the Formal Charge of
an Atom?
The Formal Charge is a mathematical summation of
the number of actual electrons associated with an
atom in a molecule. “Electronic Bookkeeping”
The Formal Charge is all determined relative to the
number of valence electrons an atom would have in
the ground state.
Remember, valence electrons are those found in the
outermost unfilled shell.
What is the Formal Charge of
an Atom?
Anytime you see a charge in a molecule, it tells you
that the atom with the charge has more or less
electrons than it normally would.
A -1 charge equals one extra electron on an atom.
A +1 charge equals one less electron on an atom.
What is the Formal Charge of
an Atom?
Charges can be found on all sorts of atoms common
to organic chemistry, including carbons, oxygens,
nitrogens and halides.
Remember that carbon typically has four covalent
bonds. If it has only three, then it will be a charged
atom, depending on whether it has a lone pair or
not.
C
C
H
O
H
What is the Formal Charge of
an Atom?
Oxygen atoms, when neutral, have two covalent
bonds and two lone pairs, like in water. Often
though oxygen atoms may have negative or positive
charges.
Nitrogen atoms, when neutral, have three covalent
bonds and one lone pair. These can also have
negative or positive charges, depending on what is
bonded.
What is the Formal Charge of
an Atom?
The presence of more or less electron density in a
molecule dictates the flow of electrons in a process
so this is really helpful information.
So – how do you calculate the Formal Charge on an
atom?
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Calculating Formal

Charges

Simple but significant

What is the Formal Charge of

an Atom?

  • The Formal Charge is a mathematical summation of the number of actual electrons associated with an atom in a molecule. “Electronic Bookkeeping”
  • The Formal Charge is all determined relative to the number of valence electrons an atom would have in the ground state.
  • Remember, valence electrons are those found in the outermost unfilled shell.

What is the Formal Charge of

an Atom?

  • Anytime you see a charge in a molecule, it tells you that the atom with the charge has more or less electrons than it normally would.
  • A -1 charge equals one extra electron on an atom.
  • A +1 charge equals one less electron on an atom.

What is the Formal Charge of

an Atom?

  • Charges can be found on all sorts of atoms common to organic chemistry, including carbons, oxygens, nitrogens and halides.
  • Remember that carbon typically has four covalent bonds. If it has only three, then it will be a charged atom, depending on whether it has a lone pair or not.

C^ C

H

O

H

What is the Formal Charge of

an Atom?

  • Oxygen atoms, when neutral, have two covalent bonds and two lone pairs, like in water. Often though oxygen atoms may have negative or positive charges.
  • Nitrogen atoms, when neutral, have three covalent bonds and one lone pair. These can also have negative or positive charges, depending on what is bonded.

What is the Formal Charge of

an Atom?

  • The presence of more or less electron density in a molecule dictates the flow of electrons in a process so this is really helpful information.
  • So – how do you calculate the Formal Charge on an atom?

What is the Formal Charge of

an Atom?

  • The equation to determine the Formal Charge on an atom: FC = (The number of valence electrons on the atom in the ground state) – ½ (total number of electrons in covalent bonds attached to the atom, with each covalent bond having two electrons) – (all electrons in lone pairs on an atom, with each lone pair equal to two electrons).
  • So:

FC = #Valence – ½ (bonding) – (all lone pair electrons)

What is the Formal Charge of

an Atom?

  • Keep in mind that Formal Charge is for a specific atom so you have to know exactly which atom you are doing the calculation for.
  • Determine the Formal Charge on the nitrogen atom in the following:

N

H H

H

Calculating some Formal

Charges

  • Nitrogen is in Group V and has 5 valence electrons in the ground state.
  • FC = #Valence – ½ (bonding) – (all lone pair electrons)
  • FC(N) = 5 – ½ (6) – (2) = 5 – 3 – 2 = 0
  • Nitrogen has no charge – its neutral.

N

H H

H

Calculating some Formal

Charges

  • Calculate the formal charge on oxygen in the hydronium ion shown:
  • Oxygen is in Group VI and has 6 valence electrons in the ground state.
  • FC = #Valence – ½ (bonding) – (all lone pair electrons)

O

H H

H

Calculating some Formal

Charges

  • FC = #Valence – ½ (bonding) – (all lone pair electrons)
  • FC(O) = 6 – ½ (6) – (2) = 6 – 3 – 2 = +

O

H H

H

Calculating some Formal

Charges

  • Every time you see that positive charge on an atom, it technically means the atom is missing one entire electron.
  • In this case, the oxygen only has five electrons, not six.

O

H H

H

Calculating some Formal

Charges

• FC(O) = 5 – ½ (8) – (0) = 5 – 4 – 0 = +

N

H

Calculating some Formal

Charges

  • Calculate the formal charge on the carbon (highlighted in red) in the molecule shown:

H 3 C

S C

H

O

H

Calculating some Formal

Charges

  • Carbon is in Group IV.
  • FC(O) = 4 – ½ (6) – (2) = 4 – 3 – 2 = -

H 3 C

S C

H

O

H

Calculating some Formal

Charges

  • Calculate the formal charge on the sulfur (highlighted in red) in the molecule shown:

H 3 C

S

CH 3

O

Calculating some Formal

Charges

  • Sulfur is in Group IV.
  • FC(O) = 6 – ½ (6) – (2) = 6 – 3 – 2 = +

H 3 C

S

CH 3

O

Calculating some Formal

Charges

  • Final Problem: Calculate the formal charge on the oxygen (highlighted in red) in the molecule shown:

H 3 C

S

CH 3

O

Calculating some Formal

Charges

  • Oxygen is in Group IV.
  • FC(O) = 6 – ½ (2) – (6) = 6 – 1 – 6 = -

H 3 C

S

CH 3

O

Formal Charges

  • Just remember: Valence Electrons minus half the bonding electrons (two per bond) minus all of the lone pair electrons (two per pair)…
  • Thanks for reading…