Let's think of a normal sentence such as "I found a book with 500 pages."

Everyone knows that we can't make its question form like

"Which book did you find with 500 pages?" because the connection between "book" and "with 500 pages" is lost. So you can't ask this question.

Now, let's say our original sentence is

"I found a book to learn about the evolution theory from."

That bold part is a phrase there and "a book" and "to learn about the evolution theory from" is attached to each other obviously. We can't separate them. So do you think that it is possible to ask its question like

"Which book did you find to learn about the evolution theory from ?"

In my opinion, this question is also totally wrong. Why? Because there is no connection between "to learn..from" and "book" anymore. They are not attached anymore. So I don't accept the idea that the last question is grammatically correct and natural in English. Do you agree with me?

closed as unclear what you're asking by FumbleFingers, J. Taylor, JJJ, David, jimm101 Jun 5 '18 at 22:58

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    "Everyone knows that we can't make its question form like "Which book did you find with 500 pages?" - this is a perfectly normal sentence. Which man did you see with three dogs? – Michael Harvey Jun 2 '18 at 11:27
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    When you got into the room whom did you find with Mr. Reynolds? Perfectly normal English, apart from the fact that most of us just use who rather than whom today. And I expect there will be at least hundreds if not thousands more examples of the construction in that link. I see no "question" here - just someone who's mistakenly picked up a false "rule". – FumbleFingers Jun 2 '18 at 11:40
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    @Jawel - what "linguistic document"? We cannot see it. – Michael Harvey Jun 2 '18 at 11:51
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    The English language doesn't prohibit asking about anything ... even about books with 500 pages. If a linguist appears to take exception to that, it may be that they are talking about something else. – Lawrence Jun 2 '18 at 11:55
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    @Jawel: I think you're splitting hairs with your syntactic breakdown there. Would you also reject Is this the only book you could find with 500 pages? I'm guessing you have a problem with that because you think the prepositional clause should appear immediately after the noun if refers to: Is this the only book with 500 pages you could find?, but I have to say that's a mistaken idea. There are many contexts where the first version would be preferred by the careful writer/speaker. – FumbleFingers Jun 2 '18 at 12:06

You are confusing/conflating two ideas:

  • whether a question is grammatically correct in English; and
  • whether a question naturally elicits a given answer.

Via links you provided in comments under your question, I found a useful example that highlights this difference:

Indirect question:
(23) a. They have forgotten which problem they should solve by Fourier analysis.
b. * How have they forgotten which problem they should solve?
- Be sure to interpret How in (23b) as modifying the complement verb solve, as indicated by the trace, not the matrix verb forgotten. In other words, a possible answer to (23b) is by Fourier analysis, but not by succumbing to Alzheimer's.
- Wh movement in English

The intended answer there was "Fourier analysis" (item 23a), but the question in item 23b doesn't elicit that answer.

Likewise, your first sample question

Which book did you find with 500 pages?

doesn't elicit the intended answer

I found a book with 500 pages.

Likewise with your second sample question. The "which book" question doesn't match the intended answer of "I found it".

However, just because a question doesn't match an intended answer, it doesn't mean that the question itself is ungrammatical. Both sample questions make sense grammatically.

The question's title asks:

Can “to do something” refer to a noun with wh question?

I take that to ask whether something like "I found it" (cf your "to do something") can refer to a noun like "a book" (cf your "noun") by asking "Which book did you find?" (cf your "with wh question").

The answer is that they are not equivalent: "I found it" isn't a noun - it's a whole statement/assertion/proposition. However, the assertion does refer to a noun ("it"), which is also used in the wh question. The answer to the wh question, however, should be a noun (or noun phrase) that is more specific than that mentioned in the question.

That is, if the question asks "Which book with 500 pages did you find?", the reply "I found a book with 500 pages." isn't a particularly satisfying answer. More acceptable answers include "I found the white book with 500 pages." or "I found the original book with 500 pages." etc. In each case, the answer narrows the universe referenced in the wh question, thereby addressing the operative part of the question, namely, the word "Which".

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