Organic Chemistry: Reaction of CH3COCl & C6H5NH2

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Discussion Overview

The discussion revolves around the reaction between ethanoyl chloride (CH3COCl) and aniline (C6H5NH2), focusing on the structural formula of the organic product formed. Participants explore the mechanism of the reaction, including the role of electrophiles and the potential positions of attack on the aniline ring.

Discussion Character

  • Homework-related
  • Debate/contested
  • Technical explanation

Main Points Raised

  • One participant suggests that ethanoyl chloride will dissociate into CH3CO(+) and Cl(-) due to polarity, questioning where the electrophile will attack on the aniline.
  • Another participant argues against the conclusion that ethanoyl chloride will break by itself, stating that a Lewis acid cannot be used as it would react with aniline. They propose that if the compound were to break, the electrophile would attack at ortho-para positions due to the activating nature of the aniline group.
  • One participant expresses doubt about the involvement of the ring in the reaction.
  • A request for clarification on the correct mechanism is made, specifically asking another participant to elaborate.
  • Another participant suggests that searching for information on aniline and acyl chloride could provide the correct answer.
  • A humorous remark is made about the expectation for elaboration from a specific participant known for brief responses.

Areas of Agreement / Disagreement

Participants express differing views on the mechanism of the reaction and the involvement of the aniline ring, indicating that multiple competing perspectives remain without a consensus on the correct approach.

Contextual Notes

There are unresolved assumptions regarding the reaction mechanism and the roles of the reactants, as well as the potential for different products based on the positions of electrophilic attack.

thereddevils
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Homework Statement



Give the structural formula of the organic product formed from the following reaction:

CH3COCl + C6H5NH2

Homework Equations





The Attempt at a Solution



The ethanoyl chloride will break into CH3CO(+) and Cl(-) due to polarity. Then, which part of the aminobenzene will the electrophile attack?
 
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I don't think you can conclude that ethanoyl chloride will break by itself. We can't use a Lewis acid for this purpose as it will react with aniline.

If you somehow break the compound, the electrophile will attack at ortho-para positions as aniline group is a ring activator (infact the reaction will be very vigorous and it over-reacts to form a tri substituted compound).
 
Last edited:
I don't think ring will be involved.
 
Thanks, so what's the correct mechanism for this? Borek, could you pls elaborate on that?
 
Just googling for aniline and acyl chloride should give you the correct answer.
 
thereddevils said:
Borek, could you pls elaborate on that?

Lol...do you expect Borek to elaborate? He always writes one liners :biggrin:
 

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