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02-23 GOC L3

The document discusses the classification of compounds into aromatic, anti-aromatic, and non-aromatic based on their structural and electronic properties, including cyclic structure, conjugation, and electron count as per Hückel's rule. It also explains resonance energy, its calculation, and the significance of resonance in stabilizing aromatic compounds. Additionally, it introduces annulenes and highlights the mesomeric effect on electron density in benzene rings.

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20 views16 pages

02-23 GOC L3

The document discusses the classification of compounds into aromatic, anti-aromatic, and non-aromatic based on their structural and electronic properties, including cyclic structure, conjugation, and electron count as per Hückel's rule. It also explains resonance energy, its calculation, and the significance of resonance in stabilizing aromatic compounds. Additionally, it introduces annulenes and highlights the mesomeric effect on electron density in benzene rings.

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tebebov907
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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SIR (Steric Inhibition in Resonance) Effect

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Aromatic compound:
Unusually stable cyclic conjugated compounds are called as aromatic
compounds.
Conditions for a compound to be aromatic:
1) Compound must have with cyclic part.
2) Compound should be with complete cyclic conjugation or complete cyclic
delocalization.
3) At least cyclic conjugation part must be in same plane (or) nearly same
plane.
4) It should follow Huckle’s rule
i.e., it should have (4n+2) 𝝅 electrons (cyclic delocalized π electrons)
where n = 0, 1, 2, 3, .…..

Examples:
Anti-aromatic compound:
Cyclic conjugated molecules, which are unstable (or very less stable)
are called as anti aromatic molecules.
It does not exist at room temperature.
Conditions for a compound to be anti-aromatic:
1) Compound must have with cyclic part.
2) Compound should be with complete cyclic conjugation or delocalization.
3) At least cyclic conjugation part must be in same plane (or) nearly same
plane.
4) Compound should have 4n𝝅 electrons (cyclic delocalized π electrons)
where n = 1, 2, 3.4…..

Example

Non-aromatic compounds:
If a compound does not follow any of the above condition then it is neither
aromatic nor anti-aromatic, so it is called a non-aromatic compound.

Example

Although cyclooctatetraene has (4n)π electrons but even then it is not an


antiaromatic. Geometry of this compound is non planar. Thus it is non aromatic.
lInd, !IIrd & IVth compounds are not completely conjugated.

Stability order:
Aromatic > Non-aromatic > Anti-aromatic.
Comparison between aromatic, anti aromatic and non-
aromatic compounds.
Characteristics Aromatic Anti Aromatic Non-Aromatic
compounds (A) compounds (B) compounds (C)
Example

1. Structure Cyclic, planar all Cyclic, planar all Cyclic or acyclic


atoms of ring sp2 atoms of ring sp2 planar, or non
hybridised hybridised planar sp or sp2 or
sp3
2. No. of π e– s in (4n + 2)π e– (4n)π e– Any no. of πe– s
the ring
(Huckle’s rule)
3. MOT Paired e– s in Some πe– in non- B.MO./Non-
B.M.O. bonding M.O. bonding M.O.
4. Overlapping Favourable over Unfavourable Simple
lapping of p over lapping of p overlapping like
orbital orbital alkenes
5. Resonance Very high Zero 4-8 kcal/mol like
alkenes
energy (R.E.) R.E. > 20-25
kcal/mol
6. Stability Have extra Unstable, not- Normal stability
stability due to exist at room like a conjugated
close temperature system
Conjugation of π
e– s
7. Characteristic Electrophilic Dimerization Electrophilic
Reactions substitution reaction to attain addition reaction
Reaction stability like alkenes
Examples:
Compound Cyclic Planar Complete Cyclic πe– Remarks
Conjugation or
delocalization

1. ✓ x x 2πe– Non aromatic

2. ✓ ✓ ✓ 2πe– Aromatic

3. ✓ ✓ ✓ 4πe– Anti aromatic

4. ✓ ✓ ✓ 4πe– Anti aromatic

5. ✓ ✓ ✓ 2πe– Aromatic

6. ✓ ✓ ✓ 6πe– Aromatic

7. ✓ x x 4πe– Non aromatic

8. ✓ ✓ ✓ 4πe– Anti aromatic

9. ✓ ✓ ✓ 6πe– Aromatic

10. ✓ ✓ ✓ 6πe– Aromatic

11. ✓ ✓ ✓ 6πe– Aromatic


12. ✓ ✓ ✓ 10πe– Aromatic

13. ✓ ✓ ✓ 6πe– Aromatic

14. ✓ ✓ ✓ 6πe– Aromatic

15. ✓ ✓ ✓ 4πe– Anti aromatic

16. ✓ ✓ ✓ 6πe– Aromatic

17. ✓ ✓ ✓ 6πe– Aromatic

18. ✓ ✓ ✓ 6πe– Aromatic

19. ✓ x x 6πe– Non aromatic

20. ✓ ✓ ✓ 6πe– Aromatic


RESONANCE ENERGY
The energy difference between most stable resonating structure and resonance hybrid is known as
resonance energy

• It's the experimental value which is calculated by heat of hydrogenation (HOH)

• Higher the value of resonance energy, greater is the resonance stabilization.

Resonance Energy of Benzene :

The resonance energy of benzene is calculated from the heat of hydrogenation as given below :

Resonance energy = (HOH)Calculated (HOH)Experimental

Resonance energy comparison


1. Consider better resonance or equivalent resonating structures, molecules having equivalent
resonating structures must have more resonance energy, than non-equivalent resonating
structures.

eg.

2. Aromatic compound have more resonance energy than non-aromatic compound.

3. In case of larger conjugation, more will be the Resonance energy.


4. Resonance energy will be more, when π-bond, lone pair conjugation is present than π, π-
conjugation
Annulene

1) Completely conjugated monocyclic hydrocarbons are called as Annulenes

2) The number in square bracket indicates the number of carbons present in the given
hydrocarbon

3) General Formula

Examples

1)
Anti Aromatic

2)
Aromatic

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3) Non Aromatic
Non planar
No resonance
Tub Shape

4)

All Structures of [10]- Annulene are Non planar.


Therefore [10]- Annulene is Non Aromatic.

Methylene Bridge [10]- Annulene

Aromatic

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5)

Anti Aromatic

6)

Aromatic

Dehydro [14]-Annulene

Aromatic

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Summary

Pyrene

It is polycyclic polyenes.

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Aromatic

Azulene

Highly Polar molecule


Dipole Moment=1.08 D
Aromatic Hydrocarbon molecule
10 ∏ electrons

In resonating structures of azulene , both ring is aromatic.

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Important Points of Mesomeric Effect

Note:

1) +M group increases electron density on benzene ring and -M group


decreases electron density on benzene ring

Q) Arrange the following in decreasing order of electron density on


benzene ring

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2) Group that show +M as well as -M effect

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3) Mesomeric effect works at only ortho & para position, it is absent on meta position, while
inductive effect works at all three position o, m, p however intensity of effect decreases as the
distance increases.
4) Mesomeric effect always dominates on inductive effect except halogen (F,Cl, Br, I, only)

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