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Question

Choose the correct option regarding the given compounds:

A
Compound (a) is the most stable
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B
Compound (c) is the most stable
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C
Compound (c) is the least stable
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D
Compound (b) is more stable than (a)
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Solution

The correct option is B Compound (c) is the most stable
For compound (a)
Cyclopentadiene:
Here one of the carbon atoms is sp3 hybridised. So, it is not planar. It is non-aromatic.
For compound (b)
Cyclopentadienyl cation:
All the carbon atoms are sp2 hybridised, and hence the structure is planar. It has conjugation and number of π e=4
It follows (4n) π e rule.
It is anti-aromatic.
For compound (c)
Cyclopentadienyl anion:
It is planar.
Has conjugation
Follows Huckel's rule (4n+2) e , since it has 6 π e
It is Aromatic.
Stability order :
Aromatic>Non-aromatic>Anti-aromatic

Hence, option (b) is correct.

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