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When nitrobenzene is treated with Br(2)...

When nitrobenzene is treated with `Br_(2)` in presence of `FeBr_(3)`, the major product formed is `m-`bromo`-`nitrobenzene. Statement which is related to obtain the `m-`isomer is

A

The electron density at the meta position is greater than those at the ortho and para positions

B

Aromaticity is lost in the `simga-`complexes formed by the attack of `Br^(+)` at the ortho and para positions but not at the meta position.

C

The `sigma-`complex formed by the attack of `Br^(+)` at the meta position is the least destablized and the most stable among the three `sigma-`complexes

D

In the final step of regeneration of benzene ring by the loss of `H^(+)` from the `sigma-`complexes, the meta-oriented `sigma-`complex loses `H^(+)` most readily

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The correct Answer is:
To solve the question regarding the formation of m-bromo-nitrobenzene when nitrobenzene is treated with Br₂ in the presence of FeBr₃, we need to analyze the reaction mechanism and the influence of the nitro group on the electrophilic aromatic substitution process. ### Step-by-Step Solution: 1. **Understanding the Reactants**: - Nitrobenzene (C₆H₄(NO₂)) contains a nitro group (-NO₂) that is a strong electron-withdrawing group due to its -M (mesomeric) effect. This means it decreases the electron density on the aromatic ring. 2. **Electrophilic Aromatic Substitution Mechanism**: - When nitrobenzene reacts with bromine (Br₂) in the presence of a Lewis acid catalyst like FeBr₃, the bromine molecule is polarized. The FeBr₃ helps to generate a more reactive electrophile, Br⁺. 3. **Formation of the Sigma Complex**: - The Br⁺ electrophile can attack the aromatic ring at three possible positions: ortho, meta, and para relative to the nitro group. - Due to the electron-withdrawing nature of the nitro group, the electron density at the ortho and para positions is reduced. This makes these positions less favorable for electrophilic attack compared to the meta position. 4. **Stability of the Sigma Complex**: - When Br⁺ attacks the meta position, the resulting sigma complex retains more electron density compared to the ortho and para complexes. This is because the positive charge generated in the ortho and para complexes is destabilized by the electron-withdrawing nitro group. 5. **Regeneration of Aromaticity**: - After the electrophilic attack, the sigma complex loses a proton (H⁺) to regenerate the aromatic system. The loss of H⁺ from the meta position is more favorable due to the higher electron density at that position. 6. **Conclusion**: - As a result of the above factors, the major product formed is m-bromo-nitrobenzene. The statement that relates to obtaining the m-isomer is that the electron density at the meta position is greater than that at the ortho and para positions due to the electron-withdrawing effect of the nitro group. ### Final Answer: The major product formed is m-bromo-nitrobenzene because the electron density at the meta position is greater than at the ortho and para positions due to the electron-withdrawing effect of the nitro group.
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ALLEN-ALKENE, ALKANE & ALKYNE -EXERCISE-2
  1. In the reaction the major product formed is :

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  2. The major product formed in the reaction is :

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  3. When nitrobenzene is treated with Br(2) in presence of FeBr(3), the m...

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  4. Isopropylbenzene can be prepared by :

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  5. Which of the following statement is true about aromatic compound?

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  6. Which among the following is a meta directing group?

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  7. How many of the following groups are ortho,para directing and ring act...

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  8. Which of the following statements are correct :

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  9. The reaction of toluene with chlorine in presence of ferric chloride g...

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  10. Explain, why does benzene not undergo addition reactions easily?

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  11. Among following statements on the nitration of aromatic compoun...

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  12. Chlorination of benzene in the presence of halogen carrier is an examp...

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  13. Benzene reacts with CH(3)Cl in the presence of anhydrous AlCl(3) to ...

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  14. Select the incorrect statement among the following

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  15. Identify the correct order of reactivity in electrophilic substitution...

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  16. The structure of Wheland intermediate obtained after the attack of Br^...

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  17. Conjugation of electron withdrawing groups, e.e., -CHO, -overset(O)ove...

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  18. Which of the following sttements is//are true

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  20. Most stable frec ratical formed at the position

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