Here are a few notes on formal charges:

 For most organic molecules, the formal charge on each atom is zero
 The most likely structure is usually that in which the formal charges have been
minimized
 If formal charges persist, negative charges should be on more electronegative elements,
and positive charges should be on less electronegative elements
 If two atoms with opposite formal charges are connected, this separation of formal charge
should be eliminated by making multiple bonds. Please note that this structural
refinement does not supersede the octet rule for row 2 elements (Figure 1.18)
 Structures in which two atoms with identical formal charges are connected are unlikely to
be an accurate representation of the molecule or polyatomic ion

Figure 1.18. Minimizing

the separation of formal charge by forming multiple bonds.

The rules above will allow you to accurately predict the two-dimensional structures and bond
orders for many main group compounds. Organic molecules are mainly comprised of row 2
elements and hydrogen, but may contain repetitive chain or ring motifs. Therefore, Step 2 may
not be applicable in some cases (Figure 1.19). As the number of atoms in the molecule increases,
the number of possible, valid Lewis structures—constitutional isomers—increases as well. Keep
these general guidelines in mind when proposing structures for organic molecules:

 Carbon atoms are usually the central atom in small organic molecules, and serve as the
repeating unit in chain and ring structures
 Formal charges in organic molecules are usually zero, and rarely exceed ±1
 For neutral organic molecules, note the following:
 Carbon makes four total bonds (never more!)
 Nitrogen makes three total bonds
 Oxygen makes two total bonds
 Halogens make one total bond
 Hydrogen makes one total bond
 Row 2 elements cannot exceed an octet of electrons

Note that all of these guidelines are followed by the structures of molecules in Figure 1.19.
 Figure 1.19. Lewis
structures for common types of organic molecules

The table below shows the general structure of charged and neutral boron, carbon, nitrogen,
oxygen and halogen organic molecules. In organic chemistry, it is very important that you are
able to identify the charge on atoms. It is part of the language.

Note: Only carbon is allowed to have a positive charge and not have a full octet. A nitrogen,
oxygen and halogen with a positive charge must have a full octet.
Table 1.4. Common formal charges in organic molecules.

Q1.8 - Level 1
Review
Confusing
Assign formal charges to the atoms in the Lewis structure below.

Select an answer and submit. For keyboard navigation, use the up/down arrow keys to select an
answer.
a
(-2)
b
(-1)
c
(0)
d
(+1)
e
(+2)

Explanation

Recall that Formal Charge = #Valence Electrons – (# non-bonding electrons + (1/2) # bonding
electrons). In this molecule, carbon has 4 valence electrons, 0 non-bonding electrons, and 8
bonding electrons. Here, the formal charge of carbon is: FC = 4 – (0 + (1/2)8), or FC = 4 – 4, or
FC = 0.

This is your recorded answer from classroom or homework

Explanation

Explanation

Recall that Formal Charge = #Valence Electrons – (# non-bonding electrons + (1/2) # bonding
electrons). In this molecule, carbon has 4 valence electrons, 0 non-bonding electrons, and 8
bonding electrons. Here, the formal charge of carbon is: FC = 4 – (0 + (1/2)8), or FC = 4 – 4, or
FC = 0.

Q1.9 - Level 1
Review
Confusing
Assign formal charges to the atoms in the Lewis structure below.

Select an answer and submit. For keyboard navigation, use the up/down arrow keys to select an
answer.
a
(-2)
b
(-1)
c
(0)
d
(+1)
e
(+2)

Explanation

Recall that Formal Charge = #Valence Electrons – (# non-bonding electrons + (1/2) # bonding
electrons). In this molecule, nitrogen has 5 valence electrons, 3 non-bonding electrons, and 4
bonding electrons. Here, the formal charge of nitrogen is: FC = 5 – (3 + (1/2)4), or FC = 5 – 5,
or FC = 0.

This is your recorded answer from classroom or homework

Explanation

Explanation
Recall that Formal Charge = #Valence Electrons – (# non-bonding electrons + (1/2) # bonding
electrons). In this molecule, nitrogen has 5 valence electrons, 3 non-bonding electrons, and 4
bonding electrons. Here, the formal charge of nitrogen is: FC = 5 – (3 + (1/2)4), or FC = 5 – 5,
or FC = 0.

Q1.10 - Level 1
Review
Assign formal charges to the atoms in the Lewis structure below.

Drag and drop options on the right-hand side and submit. For keyboard navigation...

Press space or enter to grab (+1)

 N

(+1)

Press space or enter to grab (0)

 H

(0)

Press space or enter to grab (+2)

 (+2)

Press space or enter to grab (-2)

 (-2)

Press space or enter to grab (-1)

 (-1)

Explanation

Recall that Formal Charge = #Valence Electrons – (# non-bonding electrons + (1/2) # bonding
electrons). In this molecule, nitrogen has 5 valence electrons, 0 non-bonding electrons, and 8
bonding electrons. Here, the formal charge of nitrogen is: FC = 5 – (0 + (1/2)4), or FC = 5 – 4,
or FC = +1.

Submitted:

Please enter a new answer to submit.

This is your recorded answer from classroom or homework

Please enter a new answer to submit.

Explanation

Explanation

Recall that Formal Charge = #Valence Electrons – (# non-bonding electrons + (1/2) # bonding
electrons). In this molecule, nitrogen has 5 valence electrons, 0 non-bonding electrons, and 8
bonding electrons. Here, the formal charge of nitrogen is: FC = 5 – (0 + (1/2)4), or FC = 5 – 4,
or FC = +1.

Q1.11 - Level 1
Review
Assign formal charges to the Carbon in the Lewis structure below.

Select an answer and submit. For keyboard navigation, use the up/down arrow keys to select an
answer.
a
(-2)
b
(-1)
c
(0)
d
(+1)
e
(+2)

Explanation

Recall that Formal Charge = #Valence Electrons – (# non-bonding electrons + (1/2) # bonding
electrons). In this molecule, carbon has 4 valence electrons, 0 non-bonding electrons, and 8
bonding electrons. Here, the formal charge of carbon is: FC = 4 – (0 + (1/2)8), or FC = 4 – 4, or
FC = 0.

This is your recorded answer from classroom or homework

Explanation

Explanation

Recall that Formal Charge = #Valence Electrons – (# non-bonding electrons + (1/2) # bonding
electrons). In this molecule, carbon has 4 valence electrons, 0 non-bonding electrons, and 8
bonding electrons. Here, the formal charge of carbon is: FC = 4 – (0 + (1/2)8), or FC = 4 – 4, or
FC = 0.

1.2.2C Bond-Line Drawings

Many important organic molecules, especially biologically active organic molecules, have
complex structures that are difficult to depict using Lewis structures, given the spatial constraints
imposed by using letters to represent atoms of different elements. In order to address this
difficulty, chemists have developed the bond-line drawing convention that allows organic
molecules to be drawn expediently, while minimizing the use of space. The bond-line method
makes use of the fact that most of the atoms in organic molecules are carbon and hydrogen. In
this method, carbon atoms are represented by the end-points and intersections of lines. It is
assumed that each carbon makes four bonds, any bonds not explicitly drawn are assumed to be
between carbon and hydrogen.

Perhaps the simplest way to learn how to use the bond-line method is to convert a bond line
structure to an expanded Lewis structure. Consider the molecule in Figure 1.20.

Figure 1.20. Bond-line diagram of N-(4-ethynylphenyl)-

4-fluoro-3-methylbutanamide

Step 1: Locate all of the carbon atoms. Recall that these are at the intersections and end-points of
lines.
 Figure
1.21. Locating carbon atoms in bond-line structure

Step 2: Add in hydrogens bound to carbon atoms. Unless there is a charge associated with a
carbon atom, you should assume it has four bonds. All bonds not explicitly drawn are assumed to
be between carbon and hydrogen.

Figure 1.22. Locating hydrogen atoms in bond-line structure

Step 3: Add in lone pairs. Unless there is a charge on an atom, all atoms should be assumed to
have an octet.

Figure 1.23. Locating non-bonding electrons in bond-line structure

Step 4: If charges are present on a carbon atom, you will need to remove one hydrogen atom. In
the case of a positively charged carbon, this is all you need to do. In the case of a negatively
charged carbon, you will need to recognize that there is a lone pair of electrons localized on that
carbon atom.
 Figure 1.24.
Positively and negatively charged carbons in bond-line structures

Q1.12 - Level 2
Review
What is the molecular formula for the compound below?

Select an answer and submit. For keyboard navigation, use the up/down arrow keys to select an
answer.
a

C H NO
b

C H NO
c

C H NO
d

C H NO

Explanation

Unless there is a charge associated with a carbon atom, you should assume it has four bonds. In
this structure, there are 6 carbons, 13 hydrogens, 1 nitrogen, and 1 oxygen.

This is your recorded answer from classroom or homework

Explanation

Explanation

Unless there is a charge associated with a carbon atom, you should assume it has four bonds. In
this structure, there are 6 carbons, 13 hydrogens, 1 nitrogen, and 1 oxygen.
Q1.13 - Level 3
Review
Determine the molecular formula for the compound below by correctly matching the correct
number of carbon and hydrogens.

Drag and drop options on the right-hand side and submit. For keyboard navigation...

Press space or enter to grab 10

 C

10

Press space or enter to grab 14

 H

14

Press space or enter to grab 11

 11

Press space or enter to grab 15

 15

Press space or enter to grab 13

 13

Press space or enter to grab 9

 9

Explanation