🧪AP Chemistry
8 min read•Last Updated on June 18, 2024
Dalia Savy
Anika P
Dalia Savy
Anika P
Sometimes, there is not just one way to represent a molecule with a Lewis structure. If a structure can be drawn in multiple ways, the structure is known to have resonance. A good way of thinking of resonance is like mixing paint🎨.
When you draw out the two or three resonance structures of a molecule, those two/three structures make up the entire molecule. The actual structure is represented by an average of these 2-3 structures. This can lead to bond orders that are fractions, such as bond orders of 1/3 or 2/3.
A common misconception is that structures that have resonance are truly able to exist with different bond connections. However, resonance is all about representing a molecule in varying ways just to make it clear that the molecule is actually an average of those representations in space. This will make more sense as we take a look at several examples.
Let's try drawing the lewis dot structure (LDS) of the polyatomic ion NO3-.
Recall some steps for this process that we discussed in the last study guide:
Count the number of valence electrons that the molecule has in total. Nitrogen has 5 and an oxygen atom has 6. Since there are three oxygen atoms, we must account for each: 5+6+6+6 = 23. But...NO3- is a polyatomic ion and there is a charge attached to the molecule as a whole. The -1 charge indicates that there is one more electron, so there must be a total of 24 valence electrons represented in the LDS.
Draw the central atom, which in this case, is nitrogen since there is only one nitrogen atom.
Draw the 3 oxygen atoms surrounding nitrogen and three single bonds connecting them to nitrogen. Draw the full octets:
Count the current number of valence electrons. There are 26, so somehow we have to get rid of 2 of them🤔. Remember, when there are too many electrons, we can replace a single bond and a lone pair with a double bond. In this case, if we change them all to double bonds, we won't have enough electrons! This is where resonance comes in: you only change one to a double bond.
Now we count: we have 24! This is one way to draw the lewis dot structure of NO3-. How do we know which bond to make a double bond?
Simple answer: any of them since each of the three possibilities simultaneously exist in reality. There are three ways to draw this structure on paper:
Any of these would be acceptable. On the AP Exam itself, you would be required to draw all three side by side with these specific arrows between them ↔️.
In reality, the structure doesn't have 2 single bonds and 1 double bond. It has a 4/3 bond order. There is just no way to represent 4/3s of a bond.
How did I know it was a 4/3s bond? The easiest way to know the bond order is ( # of lines / # of spaces ). There are 4 lines or bonds and 3 spaces for bonds. A 4/3s bond is between a single bond and a double bond. Therefore, it is stronger than a single bond but weaker than a double bond. A 4/3 bond is what is represented by these three structures.
As mentioned before, on the AP Exam, draw all possible structures side-by-side with double-sided arrows between each. You may also write the word "resonance" somewhere on the page to clarify what you know and break down the question for yourself.
👉Now try drawing the LDS of nitrite (another polyatomic ion). The answer is at the very end of the guide!
Formal charge is the charge assigned to an atom in a molecule, assuming that electrons in all chemical bonds are shared equally between atoms. It reflects the electron count associated with the atom compared to the isolated neutral atom. It is used to predict the correct placement of electrons.
Here is an overall diagram, but let's get into the nitty-gritty.
The easiest way to calculate the formal charge of an atom is to do (# of valence electrons - # of dots - # of dashes). This might may not be the most technical but it's the easiest way to remember it!
Look at the image above at the SCN- ion to the left and the way they calculated formal charge:
It is good to always check your calculation of formal charge since it is easy to miscount something. If anything, just check it if an element past element 14 is involved (because that is when you can break the octet rule).
Let's draw the LDS of phosphate (PO4-3):
There should be 5+6+6+6+6+3 valence electrons, so 32 total.
Draw Phosphorus in the center and 4 oxygen atoms surrounding it with single bonds and full octets:
Looking at this lewis dot structure, we count 32 valence electrons and think it is perfect! However, phosphorus is element 15 so we should be looking at its formal charge to make sure the placement of electrons is correct.
Calculating the formal charge:- P: 5 valence electrons - 0 dots - 4 bonds = +1 formal charge- O: 6 valence electrons - 6 dots - 1 bond = -1 formal charge
When we are looking at the formal charges, we want the central atom to always have a formal charge of 0 or the most electronegative atom to have a negative formal charge. A formal charge of 0 means the electrons are localized, or not moving, and that representation of the molecule is the most stable.
One way we can lower the formal charge of Phosphorus to 0 is by adding a double bond:
Now let's check formal charge once more:- P: 5 valence electrons - 5 bonds = 0 (Perfect🥳)- Top 3 Oxygen atoms: 6 valence electrons - 6 dots - 1 bond = -1- Botton oxygen atom: 6 valence electrons - 4 dots - 2 bonds = 0 Now, instead of having no atoms with a formal charge of 0, we have two atoms with a formal charge of 0. The electrons are placed correctly, resulting in a stable bond🎉.
The polyatomic ion also has resonance now, so you should draw all 4 ways of representing it and know the bonds are 5/4 order.
** Quick Tip: An easy way to check if you calculated formal charge correctly is if the sum of the formal charges = the charge of the ion.**
Since there were 3 oxygen atoms with a -1 charge, the sum is -3, which is equal to the -3 charge of the polyatomic ion.
The following questions are pieces of free-response questions that were on previous AP Chemistry exams. These exams can be found on the College Board website.
The HCO3− ion has three carbon-to-oxygen bonds. Two of the carbon-to-oxygen bonds have the same length and the third carbon-to-oxygen bond is longer than the other two. The hydrogen atom is bonded to one of the oxygen atoms. In the box below, draw a Lewis electron-dot diagram (or diagrams) for the HCO3 − ion that is (are) consistent with the given information.
They give you a large box for you to draw your answer in, but try this on your own!
S2Cl2 is a product of the reaction. In the box below, complete the Lewis electron-dot diagram for the S2Cl2 molecule by drawing in all of the electron pairs.
Two possible Lewis electron-dot diagrams for fulminic acid, HCNO, are shown below. Explain why the diagram on the left is the better representation for the bonding in fulminic acid. Justify your choice based on formal charges.
You are given the ion and its charge and asked to draw the Lewis dot structure. Taking a look at HCO3-, you should calculate that there are a total of 23 valence electrons present, plus the additional electron from the negative charge: 24.
When you draw the structure out, you should place carbon in the center as the central atom. From there, always attach the multiple oxygen atoms to the central atom. If there is a hydrogen atom, you can basically bond it to any of the oxygens.
Once you have the atoms drawn and the full octets filled in, you count 26 valence electrons. We have too many electrons, so we must replace one single bond and lone pair with a double bond. Since there are two single bonds that you could convert to a double bond, this structure has resonance!
Here is an acceptable answer:
If one were to get this question correct, two full points would be earned:
The following answer is correct and would earn you one full point:
The basis of this question is calculating formal charges, and they even give you that hint! The best representation of a structure is one where the most electronegative atom has a negative formal charge.
This part was worth two points, one for the correct calculation of formal charge and one for a correct explanation of which is the better representation.
The following is a sample response:
Bond order is the number of chemical bonds between a pair of atoms. It indicates the stability of a bond.
Term 1 of 9
Bond order is the number of chemical bonds between a pair of atoms. It indicates the stability of a bond.
Term 1 of 9
Bond order is the number of chemical bonds between a pair of atoms. It indicates the stability of a bond.
Term 1 of 9
A Lewis structure is a graphical representation used to visualize the arrangement of valence electrons around individual atoms within molecules or ions.
Valence Electrons: The outermost electrons on an atom that participate in chemical bonding.
Covalent Bonding: A type of chemical bond formed when pairs of electrons are shared between atoms.
Octet Rule: The principle stating that bonded atoms share their eight outermost electrons.
Resonance in chemistry refers to the phenomenon where a molecule or ion can be represented by two or more Lewis structures. These different structures, called resonance forms, contribute to the overall structure of the molecule.
Resonance Structure: A way that electrons can be arranged in a molecule or ion. Different resonance structures usually have the same arrangement of atoms but differ in electron placement.
Delocalized Electrons: Electrons that are spread over several adjacent atoms rather than being confined to one atom or pair of atoms. In molecules with resonance, these electrons are delocalized across all the atoms involved.
Conjugated System: A system in which atoms are linked by alternating single and double bonds, allowing for delocalization of electrons and thus enabling resonance.
A polyatomic ion is a charged particle which has two or more atoms held together by covalent bonds.
Monatomic Ion: This is an ion formed from only one atom. It's like the solo athlete in our sports analogy.
Covalent Bond: This is the type of bond that holds the atoms within a polyatomic ion together. It's like the teamwork and strategies that hold a sports team together.
Electron Configuration: This refers to the distribution of electrons among energy levels in an atom, which influences how it forms ions and bonds with other atoms. It's like the positions and roles each player takes on in our sports team.
Valence electrons are the outermost electrons in an atom that participate in chemical reactions.
Electron Shell: This is like a layer of an onion, where each shell can hold a certain number of electrons. The outermost shell is where you'll find the valence electrons.
Covalent Bond: This is when two atoms share their valence electrons, kind of like how best friends might share their favorite toys.
Ionization Energy: This is the energy required to remove a valence electron from an atom. It's like how much effort it would take for someone to pry your favorite toy out of your hands!
In molecular geometry, central atom is an atom in a molecule or ion that has bonds with two or more other atoms.
Lone Pair Electrons: These are pairs of valence electrons that are not used in bonding but belong exclusively to one atom.
Octet Rule: A rule stating that atoms lose, gain, or share electrons so as to have eight valence electrons.
VSEPR Theory (Valence Shell Electron Pair Repulsion): A model used to predict molecular shapes based on minimizing repulsion between electron pairs around a central atom.
The octet rule states that atoms tend to form bonds in such a way that they have eight electrons in their outermost (valence) electron shell, achieving the same electron configuration as a noble gas.
Ionic Bonding: This is when one atom donates one or more electrons to another atom to achieve stable octets. It's like giving your friend the last piece of cake so you both can be happy.
Stable Electron Configuration: This refers to an atom having its outermost energy level completely filled with electrons. Imagine filling up a water bottle - it's most stable and 'complete' when it's full.
Noble Gases: These are elements with naturally occurring stable octets. They're like people who are naturally balanced and content - they don't need anything else to be happy!
Bond order is the number of chemical bonds between a pair of atoms. It indicates the stability of a bond.
Single Bond: A single covalent bond that occurs when one pair of electrons is shared between two atoms.
Double Bond: A double covalent bond involves two shared pairs of electrons between two atoms.
Triple Bond: A triple covalent bond involves three shared pairs of electrons between two atoms.
The formal charge is the charge assigned to an atom in a molecule, assuming that electrons in all chemical bonds are shared equally between atoms, regardless of relative electronegativity.
Valence Electrons: These are the outermost electrons in an atom which participate in bonding. They play into calculating formal charge.
Covalent Bonds: These are bonds formed by sharing electron pairs between atoms. The concept relates to how we calculate formal charge as we assume these shared electrons are evenly distributed for this calculation.
Lewis Structures: These diagrams represent molecules showing all valence electrons which help us visualize and calculate formal charges.
An electronegative atom has high affinity for attracting electrons towards itself within a chemical bond.
Electronegativity: This is a measure of how strongly atoms can attract bonding electrons to themselves.
Polar Bonds: These are bonds where electrons are unevenly distributed due to differences in electronegativity.
Nonpolar Bonds: These are bonds where electrons are evenly distributed because atoms have similar electronegativities.