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

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Chlorination of diphenylether using Cl2 and FeCl3 typically results in products with chlorine substituents in the ortho and para positions due to the directing effects of the ether's oxygen. The discussion clarifies that while the solutions manual indicates potential disubstitution, it is reasonable to assume monosubstitution for test purposes unless specified otherwise. The amount of Cl2 present influences the extent of chlorination, with more chlorine leading to possible disubstitution. Therefore, in an exam context, it's advisable to focus on monosubstitution unless additional reagents are indicated. Understanding the directing effects of substituents is crucial for predicting the products accurately.
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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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