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How does the halogen atom in haloarenes influence the position of further substitution in electrophilic reactions?

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The halogen atom in haloarenes, being o, p-directing, directs further substitution to the ortho- and para-positions with respect to itself due to resonance, resulting in increased electron density at these positions.

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  1. The halogen atom in haloarenes influences the position of further substitution in electrophilic reactions through its directing effect. Halogens, being electron-withdrawing groups, deactivate the benzene ring towards electrophilic attack. However, they also exhibit a directing effect based on their position. Ortho-para directing halogens (like -Cl and -Br) direct incoming electrophiles to the ortho and para positions due to resonance stabilization and increased electron density at those positions. In contrast, meta-directing halogens (like -F) direct electrophiles to the meta position. This directing effect is crucial for predicting and understanding the regioselectivity of electrophilic aromatic substitution reactions in haloarenes.

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