Huckel Rule of Aromaticity 2 PDF

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Huckel’s rule for aromaticity

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Huckel’s rule for aromaticity
In 1931, German chemist and physicist Erich Hückel

proposed a theory to predict if a planar ring molecule
would be aromatic or not. His rule states four criteria, a
molecule should follow in order to be aromatic
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Four Criteria for Aromaticity
1. The molecule must be cyclic (a ring of atoms)
Cyclic Acyclic
Benzene (Z)-1,3,5 hexatriene
Aromatic Non Aromatic
2. The molecule must be planar or flat.
Non Aromatic Aromatic

Annulene
In above case [10]-annulene, even though it is cyclic and has (4n+2) Pi electrons (10), it is not planar due
to the repulsions between hydrogen’s and therefore it is non aromatic but if we replace two hydrogen
with CH2 bridge as in the later case, it attains planarity and all Pi electrons are in conjugation and the
molecule becomes aromatic.
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3. The molecule must be fully conjugated and it should have p orbitals at every atom in the ring.
-
All atoms are conjugated Carbon is not conjugated (SP3)
All atoms are conjugated Carbon is not conjugated (SP3)
-
-
-
All atoms are in conjugation
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4. The molecule must have 4n+2 π electrons (Where n= 0, 1, 2…) So aromatic compounds will have 2, 6,
10, 14, 18, 22, 26 ….Pi electrons.
e.g . Naphthalene as per Hückel ‘s rule

4n+2 π e- (where n=2)
4 x 2+2= 10 π e-
Pyridine Naphthalene Indole
6 Pi electrons 10 Pi electrons 10 Pi electrons
Note- If a molecule satisfies first three criteria and if it has 4n π electrons (i.e. 0, 4, 8, 12, 16…) than the molecule will be
anti aromatic. And if it is non planar, it said to be non aromatic.
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How to calculate π (Pi) Electrons in a molecule
✓ Each double bond always contributes 2 π electrons.
✓ Benzene has 3 double bonds, so it has 6 π electrons.
✓ Similarly Naphthalene and Phenanthrene have 10 and 14 pi electrons.
Benzene Naphthalene Phenanthrene

3 double bonds 5 double bonds 7 double bonds
6 Pi electrons 10 Pi electrons 14 Pi electrons
How to calculate π (Pi) Electrons in a Aromatic ions
✓ Huckel's Rule is applied to all molecules which obeys the criteria of aromaticity
✓ In cyclopentadienyl anion there are two double bonds (which contributes 4π e- ) and one
negative charge (contributes 2π e-) so it contains 6π e- and It fulfills the Huckel rule
✓ In Tropylium ion contains 3 double bonds (which contributes 6π e- )and positive charge
contains empty p orbital conjugated in the ring so It fulfills the Huckel rule and it is aromatic
✓ If an atom has one or more lone pairs of electron and is attached to a sp2 hybridized atom,
then that atom is also SP2 hybridized.
Tropylium ion Cyclopentadienyl ion

6 Pi electrons 6 Pi electrons
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How to calculate π (Pi) Electrons in a Heterocyclic Aromatic Compounds
✓ For heterocyclic molecule only difference is one or more carbons are replaced with heteroatoms like
oxygen, Nitrogen or Sulphur.
✓ In pyridine 3 conjugated double bonds contributes 6π e- and lone pair on nitrogen is not involved in
delocalisation in the ring. Similarly in cinnoline contains 10π e-.
✓ In indole there are 4 double bonds contributes 8π e- and lone pair on nitrogen atom is delocalised in
the ring and contributes 2π e- so it contains 10π e- and obeys Huckel's rule of aromaticity.
✓ In Furan one of the lone pairs of electrons on oxygen atom is delocalised in the ring and creating the
(4n+2) π e- .
Pyridine cinnoline Indole Furan

6 Pi electrons 10 Pi electrons 10 Pi electrons 6 Pi electrons
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How many Pi electrons are in the following molecules? Are they aromatic or not?
.. ..
1 2 3
The benzene anion (fig-1) has a lone pair on one of the carbons. This lone pair can’t be in a p orbital, since
the p-orbital is participating in the pi system. Instead, it’s at 90 degrees to the pi system, in the plane of the
ring.
In other words, the lone pair on carbon doesn’t count as a pair of pi electrons since it can’t overlap with the
pi system. Thus it has only 6 Pi electrons it is aromatic.
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.. ..
1 2 3
The same is also true for pyridine (fig-2), where the lone pair is also at right angles to the pi system and
therefore pyridine is aromatic with 6 pi electrons.
11
..
1 2 3
For imidazole (Fig-3) only one pair of electron on one of the nitrogen towards pi system whereas other lone
pair is at 90°C to the Pi system and do not contribute towards pi system. Therefore it has 6 Pi electrons and it
is aromatic.
Antiaromaticity
8 pi electron 12 pi electron 4 pi electron

Anti Aromatic Anti Aromatic Anti Aromatic
✓ Antiaromaticity is a characteristic of a cyclic molecule with a π electron system that has higher energy
due to the presence of 4n electrons in it
✓ For a compound be anti aromatic it has to planar, cyclic, continuous overlap of p orbital’s and should
have 4n π electrons. i.e. (4, 8 ,12, 16…)
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Homoaromaticity
✓ Homoaromaticity, in organic chemistry, refers to a special case of aromaticity in which conjugation is

interrupted by a single sp3 hybridized carbon atom.
✓ Although we say it conjugation is interrupted by sp3 carbon it is either above or below the plane and
does not really affect the p orbital overlapping.
✓ In the following fig, Tropylium ion is aromatic but on insertion of CH2 group it becomes homotropylium
ion which is homoaromatic in nature.
Non Aromaticity
✓ Non aromatic compound is either non cyclic or non planar and doesn’t necessitate a continuous form of overlapping
ring of p orbitals.
✓ It has tub shape and it is not planar, therefore it is non aromatic and not anti aromatic.
Question based on aromaticity concept , from NET, GATE, IIT JAM and SET Exams.
Correct match for the products of the reactions in Column A with the properties in Column B is
2K P aromatic
i .
1. i – P, ii – S, iii – R, iv – Q
ii Q antiaromatic 2. i – P, ii – R, iii – Q, iv – S
3. i – Q, ii – R, iii – S, iv – P
4. i – S, ii – Q, iii – R, iv – P
Heat non-aromatic
iii R
iv 2K S Homoaromatic
DEC-2016 NET
Answer
2K 2 e- 2 K+
i
aromatic (10 pi electron) (P)
ii
Homoaromatic (S)
Correct answer-A
Heat
iii
non-aromatic (R)
iv 2K 2 K+
2 e-
antiaromatic (16 electron) Q DEC-2016 NET
Question &Answer
Q-2 The compound that is antiaromatic is
I II III iv
1. I
Ans) I
2. II
Explanation- I is antiaroamtic with 4 pi electrons, where as II
3. III and III are non aromatic where as iv is aromatic with 2pi
4. IV electrons.
Dec-2014 NET
Question & Answer
-
-
A B C
Among the ions A, B and C given:

A) A is aromatic, B is homoaromatic, and C is anti aromatic.
B) A is homoaromatic, B is aromatic, and C is anti aromatic.
C) A is aromatic, B is anti aromatic, and C is homoaromatic.
D) A is homoaromatic, B is anti aromatic, and C is aromatic
Ans) B
Explanation-A is homoaromatic as it has 6 pi electron and continuous p orbital overlap is hampered
by one sp3 carbon. B is aromatic with 6 pi electrons and C is anti aromatic with 8 pi electrons.
MHA SET -2016 Paper -3
Question & Answer
-
-
I II
I and II are
(A) Both aromatic
(B) Antiaromatic and aromatic
(C) Aromatic and antiaromatic
(D) Both antiaromatic
Ans- C
Explanation- I is aromatic with 6 pi electron and II is
K-SET 2017PAER-3
antiaromatic with 8 pi electron.
Question & Answer
Which of the following are aromatic?
i) ii) A) i and ii are aromatic

B) ii and iv are aromatic
C) i, ii and iii are aromatic
D) i, iii and iv are aromatic
- Correct answer-A
iii) iv)
-
Ans) B
Explanation- ii and iv are aromatic with 2 and 6 Pi electrons respectively, whereas i is anti aromatic with 4 pi
electron as B provides empty P orbital but does not have any Pi electron to contribute. iii is anti aromatic
with 8 pi electrons.
K-SET-2015-paper-3
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Question & Answer
Which of the following statement is correct with respect to the following structures?
a) b) A) b and d are aromatic; a and c are antiaromatic
B) b and c are aromatic; a and d are antiaromatic
Correct
C) a and d are aromatic; b and answer-A
c are antiaromatic
-
c) d) D) a and c are aromatic; b and d are antiaromatic
Ans) D
Explanation – a and c are aromatic with 2 and 6 pi electrons(4n+2) and b and d are anti
aromatic with 4 and 8 pi electrons (4n).
K-Set (2015-paper-2)
22
Question & Answer
Among the following number of aromatic compounds is ____
1 2 3 4 5
Ans) 4
Explanation- Compound 1, 2, 4 and 5 are aromatic with 6 pi electrons, where as compound 3 is antiaromatic.
IIT JAM CYC-2017
23
Question & Answer
Among the following, the number of molecules that are aromatic is __
1 2 3 4
Ans) 3
5 6 7 8
Explanation- Compound-3, 6 and 8 are aromatic with 10, 10 and 14 electrons respectively, where as
compound 2 is non aromatic as it in tub shape and not planar. Compound 7 is also non aromatic as it also not
planar, where as compound 1, 4, 5 are anti aromatic with 8, 12, and 4 pi electrons respectively.
IIT JAM CYC-2016
24
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Free MCQ Tests All India Rank

In depth Solution Ask doubts

Quality notes Exam update

Huckel’s rule for aromaticity

In 1931, German chemist and physicist Erich Hückel

Non Aromatic Aromatic

All atoms are in conjugation

e.g . Naphthalene as per Hückel ‘s rule

6 Pi electrons 10 Pi electrons 10 Pi electrons

✓ Benzene has 3 double bonds, so it has 6 π electrons.

✓ Similarly Naphthalene and Phenanthrene have 10 and 14 pi electrons.

Benzene Naphthalene Phenanthrene

Tropylium ion Cyclopentadienyl ion

Pyridine cinnoline Indole Furan

8 pi electron 12 pi electron 4 pi electron

✓ Homoaromaticity, in organic chemistry, refers to a special case of aromaticity in which conjugation is

aromatic (10 pi electron) (P)

antiaromatic (16 electron) Q DEC-2016 NET

Q-2 The compound that is antiaromatic is

Among the ions A, B and C given:

i) ii) A) i and ii are aromatic

a) b) A) b and d are aromatic; a and c are antiaromatic

B) b and c are aromatic; a and d are antiaromatic

Among the following number of aromatic compounds is ____

IIT JAM CYC-2017

Among the following, the number of molecules that are aromatic is __

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