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Which halogen best delocalises electron density to benzene ring ?

 The smaller the size of halogen atom, smaller will be C-X bond. Also shorter the C- X bond, more effective wiII be overlap of p-orbitals, and more extensive will be delocalisallon. Hence fluorine effectively delocalised it's lone pairs electron with benzene ring due to smallest and most electronegativity.
Therefore order of best delocalisation of electron density to benzene ring should be.
                                  “   F > Cl > Br > I “
+M effect of fluorine is dominated over its -I effect while -I effect of other halogens is dominated over its + M effect.

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