What Are the Products of Chlorinating Diphenylether with Cl2 and FeCl3?

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Discussion Overview

The discussion revolves around the chlorination of diphenylether using Cl2 and FeCl3, focusing on the products formed and the conditions affecting substitution patterns. Participants explore the implications of reagent amounts on the substitution process.

Discussion Character

  • Homework-related, Conceptual clarification, Debate/contested

Main Points Raised

  • One participant notes that the solutions manual indicates products with chlorine in the para and ortho positions, suggesting disubstitution may occur.
  • Another participant emphasizes that the amount of chlorine present influences the outcome, questioning whether the problem implies exhaustive chlorination.
  • A participant suggests that for test scenarios, it may be prudent to assume monosubstitution unless indicated otherwise, while also acknowledging the possibility of disubstitution with excess reagent.
  • One participant agrees with the approach of assuming monosubstitution as a default strategy.

Areas of Agreement / Disagreement

Participants generally agree that the amount of chlorine affects the substitution pattern, but there is no consensus on whether to assume monosubstitution or to consider disubstitution as a possibility.

Contextual Notes

The discussion highlights the dependence on the amount of Cl2 provided and the implications of this on the expected products, but does not resolve the specifics of the chlorination process.

metalmagik
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Homework Statement


Show the product(s) of chlorination (Cl2, FeCl3) of diphenylether


Homework Equations


None


The Attempt at a Solution


My solutions manual shows products with Chlorine in the para position, and then the ortho position, with a note saying (followed by disubstitution)

I'm really just looking for some clearing up to this answer. I understand that the oxygen in diphenylether is an ortho/para director, therefore placing Chlorine in the ortho and para position. However, I just assumed this would happen on both phenyl rings. Does it depend on exactly how much Cl2 is provided?
 
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Yes it does matter how much chlorine is present. The question didn't ask about exhaustive chlorination, did it?
 
Nope! It simply put Cl2/FeCl3.

So if given that on a test it's best to assume only monosubstitution? Maybe noting possible disubstitution if more reagent is present?
 
That's the way I'd play it.
 

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