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Nitro benzene reacts with Me-overset(O)o...

Nitro benzene reacts with `Me-overset(O)overset("||")(C)-Cl` in presence of `AlCl_(3)` to produce m- nitroacetophenone.
Statement-2 : `NO_(2)` group attached to the ring is a meta directing during `S_(E)`.

A

Statement-1 is true, statement-2 is true and statement-2 is correct explanation for statement-1

B

Statement-1 is true, statement-2 is true and statement-2 is NOT correct explanation for state- ment-1

C

Statement-1 is true, statement-2 is false

D

Statement-1 is false, statement-2 is true

Text Solution

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The correct Answer is:
To solve the problem, we need to analyze the reaction of nitrobenzene with acyl chloride in the presence of aluminum trichloride (AlCl3) and understand the directing effects of the nitro group on the aromatic ring. ### Step-by-Step Solution: 1. **Identify the Reactants and Conditions**: - The reactants are nitrobenzene (C6H5NO2) and acyl chloride (Me-C(=O)-Cl). - The reaction occurs in the presence of a Lewis acid, aluminum trichloride (AlCl3). 2. **Formation of the Electrophile**: - Acyl chloride reacts with AlCl3 to form an acylium ion, which is a strong electrophile. - The reaction can be represented as: \[ \text{Me-C(=O)-Cl} + \text{AlCl}_3 \rightarrow \text{Me-C(=O)}^+ + \text{AlCl}_4^- \] - The acylium ion (Me-C(=O)+) is the active electrophile that will react with the aromatic ring. 3. **Understanding the Nitro Group's Effect**: - The nitro group (NO2) is a strong electron-withdrawing group due to its -M (meta-directing) and -I (inductive) effects. - This electron-withdrawing nature decreases the electron density on the aromatic ring, particularly at the ortho and para positions. 4. **Resonance Structures of Nitrobenzene**: - The resonance structures of nitrobenzene show that the positive charge is generated at the ortho and para positions, making them less nucleophilic. - The meta position retains more electron density compared to ortho and para, making it more favorable for electrophilic attack. 5. **Electrophilic Aromatic Substitution**: - Due to the electron-withdrawing effect of the nitro group, the electrophile (acylium ion) will preferentially attack the meta position of the nitrobenzene. - Thus, the product formed will be m-nitroacetophenone. 6. **Conclusion on Statements**: - **Statement 1**: The reaction of nitrobenzene with acyl chloride does not undergo Friedel-Crafts acylation due to the strong electron-withdrawing nature of the nitro group. Thus, Statement 1 is **false**. - **Statement 2**: The nitro group is indeed a meta-directing group during electrophilic substitution. Thus, Statement 2 is **true**. 7. **Final Answer**: - The correct option based on the analysis is that Statement 1 is false and Statement 2 is true.
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MOTION-AROMATIC COMPOUND-Exercise - 2 (Level-II)
  1. Conjugation of electron withdrawing groups, e.g., -CHO, -overset(O)ove...

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  2. Which of most reactive towards nucleophilic aromatic substitution.

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  3. Nitro benzene reacts with Me-overset(O)overset("||")(C)-Cl in presence...

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  4. Which of the following is ortho-para directing group

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  5. The structure of the compound that gives a tribromo derivative on trea...

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  6. Amongst the following, moderately activating groups is

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  7. Which of the following is ortho para directing

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  8. Of the species PhSH, Ph underset(O)underset("||")(S)R, ph underset(O)u...

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  9. Which of the following group(s) activate the benzene ring towards elec...

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  10. Statement-1 : Rate of nitration is C(6)H(6) cong C(6) D(6) cong C(6)T(...

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  11. Product (A) will be

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  12. Product (A) is

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  13. Which aromatic compound is obtained when noctane undergoes catalytic h...

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  14. Benzoic acid may be prepared by the oxidation of:

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  15. Isopropylbenzene can be prepared by :

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  16. In which of the following reaction t-butylbenzene is formed:

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  17. Product is

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  18. Which of the following reactions of bezene proves the presence of thre...

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  19. Electrophile NO(2)^(o+) attacks the following in which cases NO(2)^(o...

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  20. The reaction of replacement of a hydrogen atom in benzene by alkyl gro...

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