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

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SUMMARY

The chlorination of diphenylether using Cl2 and FeCl3 results in products where chlorine atoms are predominantly positioned at the ortho and para sites on the phenyl rings. The presence of the oxygen atom in diphenylether acts as an ortho/para director, facilitating substitution at these positions. The extent of chlorination is influenced by the amount of Cl2 available; however, for examination purposes, it is advisable to assume monosubstitution unless specified otherwise. Disubstitution may occur if excess chlorine is present, but this is not the primary focus of the question.

PREREQUISITES
  • Understanding of electrophilic aromatic substitution
  • Knowledge of directing effects of substituents in aromatic compounds
  • Familiarity with chlorination reactions involving Cl2 and FeCl3
  • Basic concepts of organic chemistry, particularly regarding diphenylether
NEXT STEPS
  • Study the mechanism of electrophilic aromatic substitution in detail
  • Research the effects of substituents on aromatic ring reactivity
  • Learn about the role of Lewis acids like FeCl3 in chlorination reactions
  • Explore the concept of disubstitution in aromatic compounds with varying reagent concentrations
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Chemistry students, organic chemists, and educators looking to deepen their understanding of chlorination reactions and the behavior of diphenylether in electrophilic aromatic substitution.

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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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