Stop Looking For “n” In A Molecule, Because You’re Looking For The Wrong Thing
The other night a student came to me with a question about aromaticity.
“There’s one thing I don’t get”, she said. “They say a molecule has to have 4n+2 electrons to be aromatic. How do you find ‘n’ ?”
Teachable moment!
These are aromatic molecules containing (4n+2) pi electrons, where “n” is a natural number
Count the pi-electrons - don’t look for “n” !
In the [4n+2] Rule (“Huckel’s Rule”), “n” Is Not A Characteristic of The Molecule!
“n” is not a characteristic of the molecule! Let me explain.
In order for a molecule to be aromatic, it has to have the following characteristics:
- It must be cyclic
- It must be conjugated (i.e. all atoms around the ring must be able to participate in π-bonding through resonance)
- It must be flat
And, it must have a certain number of π-electrons. This is known as Huckel’s rule. The number of π electrons must equal one of the numbers in this series:
2, 6, 10, 14, 18….and so on. For example, we can find aromatic molecules with 2 pi electrons, 6 pi electrons, 10 pi electrons, 14 pi electrons, 18 pi electrons, and so on.
But we have never found aromatic molecules with 0, 1, 3, 4, 5, 7, 9, 11, 12, 13, 15, 16, 17 (and so on) pi electrons. Those numbers are not in the series.
To reprise: the number of pi electrons in an aromatic molecule will always be found in the series [2, 6, 10, 14, 18 …and so on]
However, there has to be a better way of expressing it than [2, 6, 10, 14, 18… and so on”]. Right?
Question for Huckel's Rule: What Does 4n+2 Mean?
Try yourself:
How can a molecule be considered aromatic?Explanation
- A molecule can be considered aromatic if it meets the following criteria:
- It must have a cyclic structure.
- It must be conjugated, meaning that all atoms around the ring can participate in ?-bonding through resonance.
- It must have a flat structure.
- It must contain a certain number of ?-electrons, which follows Huckel's rule.
- According to Huckel's rule, the number of pi electrons in an aromatic molecule will always be found in the series [2, 6, 10, 14, 18... and so on].
- Therefore, option B is the correct answer as it accurately describes the characteristics of an aromatic molecule.
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There is! This is where we use algebra. This is where n is going to come in – we are going to use math (algebra) to replace “2, 6, 10, 14, 18… and so on” with a condensed formula.
2, 6, 10, 14, 18… is an example of an algebraic series.
Algebraically, you can express this with the formula (4n +2), where n is a natural number (0, 1, 2, 3…)
Let’s plug in different values of n (we will put n in bold)
For the formula 4n + 2
- For n = 0, we get (4 × 0 + 2) = 2
- For n = 1, we get (4 × 1 + 2) = 6
- For n = 2, we get (4 × 2 + 2) = 10
- For n = 3, we get (4 × 3 + 2) = 14
- For n = 4, we get (4 × 4 + 2) = 18
We can keep going, but do you get the idea?
By using the formula [4n +2], we are expressing the same idea as [2, 6, 10, 14, 18… and so on] but it is a lot more condensed – and precise.
Summary: “n” Comes From Algebra, NOT From Chemistry
Molecules that have the 3 characteristics listed above (cyclic, conjugated, flat) and have this number of π electrons [4n +2] will be aromatic.
The letter “n” is not a characteristic of the molecule!
Question for Huckel's Rule: What Does 4n+2 Mean?
Try yourself:
What is the algebraic expression for the series 2, 6, 10, 14...?Explanation
- The given series is 2, 6, 10, 14...
- To find the algebraic expression for this series, we can use the formula (4n + 2), where n is a natural number.
- Let's plug in different values of n into the formula:
* For n = 0, (4 ? 0 + 2) = 2
* For n = 1, (4 ? 1 + 2) = 6
* For n = 2, (4 ? 2 + 2) = 10
* For n = 3, (4 ? 3 + 2) = 14
- Based on this pattern, we can see that the correct algebraic expression for the given series is (4n + 2).
- Therefore, the correct answer is Option B.
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