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The question is about what happens to phrases during the time of making them questions.

We know that the following sentence is a normal English sentence which is correct grammatically.

  • He found a friend to study with.

The bold part in the sentence is a phrase and "to study with" refers to "a friend". That's why it would be wrong to say "To study with, He found a friend".

The problem starts here. While asking a question, we have to separate them from each other and according to many linguistics, phrases separated in a question form don't refer to each other anymore, and those questions are generally wrong.

Do you think that the following questions are correct?

Who did he find to study with?
Which friend did he find to study with?

I am not sure but my English teachers (native) said that they were awkward. Because there is "to study with" but there is no noun next to it. Why do they consider these sentence structures incorrect only as questions?

(Here, I am sharing with you a link which prohibits those kinds of questions such as "What did you sell a book about?" because of the same problem. http://www.ling.upenn.edu/~beatrice/syntax-textbook/ch12.html)

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  • This isn't really a question to be answered by linguists (who often aren't an impartial bunch w.r.t. judgements), but a question to be answered by native speakers. I'd make a questionnaire and have people answer it. – WavesWashSands Jun 2 '18 at 14:16
  • @WavesWashSands but the problem with native speakers is that they can't usually give a proof or technical explanation. That question is really technical and I need to know why those questions are correct or wrong. – Jawel Jun 2 '18 at 14:22
  • Your question was 'Do you think that the following questions are correct?'. This is exactly the kind of question that should first be posed to native speakers, not to linguists. You need the data from native speakers first, then proceed to the technical explanation of the data. Linguists don't decide whether sentences are grammatical are not; otherwise they'd be doing prescriptive grammar, not linguistics. – WavesWashSands Jun 2 '18 at 14:30
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    English relative infinitives are a very tough syntactic phenomenon. I know too many things about them but not enough about how to put the facts together. – jlawler Jun 2 '18 at 17:03
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    Infinitival relative clauses like your "to study with" typically have a modal meaning comparable to that expressed in finites by can or should. Compare He found a friend he could study with. – BillJ Jun 3 '18 at 9:44

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