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Sentence:

You should apply the cream which was prescribed by the doctor who has a better reputation to your skin.

Question: I am wondering if it's okay to have multiple adjective clauses in one sentence, and does adjective clause have any effect on the structure of the sentence(in terms of grammar).

Also, if the sentence will be grammatically correct if I change it into:

You should apply the cream which was prescribed by the doctor of/with better reputation to your skin.

In this case, I am wondering if the prepositional phrase is used correctly, and which preposition (with or of) works better in the context.

  • "better reputation to your skin" does not make any sense. Something (a product) can be good for your skin. – Lambie Sep 29 '18 at 15:37
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This kind of sentence represents a gray area. Both your examples are likely to be accepted by some native speakers but not accepted by some others. This is even a topic of continued academic research.

The problem is that even people who accept the sentence are likely to have to slow down when they read it. So in general, if you want to write clearly, you should avoid this gray area of acceptability. I can see your point that the second version (with "of") might be slightly better than the first version (with "who") but it's still not clear enough for general use.

Possible ways to refactor the sentence could be:

You should apply the skin cream which was prescribed by the doctor who has a better reputation.

You should only apply prescription skin cream if a well-reputed doctor prescribes it for you.

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