Chlorine is an electron withdrawing group and yet it is ortho- and para- directing in electrophilic aromatic substitution reaction. Why is it so?

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Becoz chlorine withdraw electron during inductive effect and release electron during participation in resonance.

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Coz of resonance , the electron density increases more at o- and p-positions as there is a negative charge either at o- and p- positions

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Electron withdrawing nature due to ...- ve I effect ...n ...ortho para nature.   due to conjugation of their lone pair....n in both conflict ...the conjugation of lone pair wins

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Chlorine as an Electron Withdrawing Group

Chlorine is indeed an electron withdrawing group due to its high electronegativity. It has a strong pull on the electrons in the molecule, which makes it capable of withdrawing electron density from the aromatic ring. This electron withdrawal effect is a result of the chlorine atom's ability to stabilize negative charge or partial negative charge through its electronegativity.

Ortho- and Para- Directing in Electrophilic Aromatic Substitution

Despite being an electron withdrawing group, chlorine is ortho- and para- directing in electrophilic aromatic substitution reactions. This means that it directs the incoming electrophile to the ortho and para positions of the aromatic ring, rather than the meta position. There are several factors that contribute to this behavior:

1. Resonance Stabilization: The ortho and para positions in the aromatic ring allow for resonance structures that involve the chlorine atom. Resonance stabilization is important in determining the reactivity of the aromatic ring towards electrophilic substitution reactions. The resonance structures with the chlorine atom in the ortho and para positions help stabilize the positive charge that is formed during the reaction, making these positions more favorable for electrophile attack.

2. Steric Effects: Steric effects also play a role in determining the regioselectivity of electrophilic aromatic substitution reactions. The chlorine atom is relatively large and can exert steric hindrance on the meta position, making it less accessible for electrophile attack. The ortho and para positions, on the other hand, are relatively free from steric hindrance, allowing for easier electrophile addition.

3. Inductive Effects: Although chlorine is an electron withdrawing group, it also has a weak inductive effect. The inductive effect of chlorine can stabilize positive charge at the ortho and para positions, further enhancing the reactivity of these positions towards electrophilic attack.

Conclusion

In conclusion, chlorine is an electron withdrawing group due to its high electronegativity. However, in electrophilic aromatic substitution reactions, it exhibits ortho- and para- directing behavior. This behavior can be attributed to resonance stabilization, steric effects, and weak inductive effects. The combined influence of these factors allows chlorine to direct the incoming electrophile to the ortho and para positions of the aromatic ring.

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