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Question

Which of the following is the correct order of electron density on the benzene ring in the following compounds?

A
I>II>III
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B
II>III>I
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C
I>III>II
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D
III>II>I
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Solution

The correct option is A I>II>III
In case of Halogens, I effect dominates over M effect. Hence they are electron-withdrawing in nature. The overall withdrawing power of Cl is more than F when attached to conjugated system even though F is more electronegative.

Cl has three effects +M,M,I . In case of Cl, +M weakens up due to 2p3p overlapping (leading to pi bond). But it is not so in case of F which involve to 2p2p overlap which is more effective. So, +M effect of F is more than Cl.

Therefore, the correct order of electron density is:
I>II>III

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