3

As I know, we can say:

  1. He asks whether she bought what?
  2. He asks what did she buy?

But we cannot extract "what" from the embedded question introduced by "whether":

  1. What does he ask whether she bought?

Thus I wonder if we can do so from the question with inversion:

  1. What does he ask did she buy?
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13
  • It seems like you need some orientation and direction on how to form indirect questions. Given that all four of those example sentences are poorly written and several of them are even ungrammatical, I'm going to pass your question over to our sister site for English Language Learners on your behalf so that you can get better attention tailored to a learner’s needs.
    – tchrist
    Sep 23, 2017 at 14:44
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    Despite the comment from @tchrist, the question is not about indirect questions. See McCawley's discussion of questions with multiple question words in The Syntactic Phenomena of English. I find the grammaticality of example 4. unclear.
    – Greg Lee
    Sep 23, 2017 at 16:14
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    Well, for starters we can't say "He asks whether she bought what?" That's not grammatical. So it's difficult to determine what exactly you are trying to say. "He asked whether she bought anything," "He asked what she bought." etc
    – Andrew
    Sep 23, 2017 at 17:16
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    @AharonM.Vertmont It would be phrased as two separate questions, "he asked if she bought anything, and if so, what (she bought)."
    – Andrew
    Sep 23, 2017 at 17:26
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    @AharonM.Vertmont For McCawley's treatment of questions, look at books.google.com/… and click once on the previous tab to get to page 488.
    – Greg Lee
    Sep 23, 2017 at 20:47

1 Answer 1

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1

I don't want to get into a discussion of "head-movement". There are contributors to this forum who could discuss this with you intelligently, but such discussions belong, IMO, on linguistics.stackexchange.com

whether heads a choice between two declarations, one of which can be implicit, the negation of the first. 

I want to know
  whether
     {you eat shellfish} 
     or 
     {not}. [i.e. you do not eat shellfish]

An unanswered interrogative is not a declaration:

He asks whether she bought what? ungrammatical

He asks whether what did she buy? ungrammatical

He asks whether did she buy it? ungrammatical

He wants to know
   whether
      what she bought  was expensive 
      (or)
      (not) [what she bought was not expensive]

P.S. Your example:

What does he ask did she buy?

We can ask questions about a question. We can ask the questioner directly or, as in your example, we can ask someone who has heard the question. Your question can also be understood as a question directed to someone who has paraphrased an original question. An idiomatic way to ask a question about a question, or about a paraphrased question, is to restate the question as a declaration with questioning intonation on the part you did not hear or on the part you need repeated, as signified below by italics and a superscript question mark:

Who ate the last cookie? original question

He wants to know who ate the last cookie. paraphrase

He wants to know who ate what ? He wants to know who did what ? to the last cookie?

What time does the train arrive? original question

He asked what time the train arrives. paraphrase

He wanted to know what time what ? arrives?
He wanted to know what time the train does what ?

When was he born?

He wants to know when you were born.

He wants to know when I was what ? He wants to know when who? was born?

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