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The sentence 'I saw the man in the room' is ambiguous (either I was in the room and saw a man, or the man was in the room and I saw him)

If we transform it into a wh-question, 'In which room did you see the man?', the sentence is no longer ambiguous. According to the structural preservation principle, transformation does not change the meaning of the sentence. Why is this the case?

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    The question is also ambiguous.
    – Keelan
    Commented Nov 10, 2022 at 12:21
  • Yes. I didn't think the question was ambiguous at first, but I thought of the parallel question In which box did you find the present?
    – Colin Fine
    Commented Nov 10, 2022 at 16:23
  • "I saw the man in the room." doesn't tell us where you were where you were when you saw him. Whether you were outside or inside, you still saw him in the room.
    – Lambie
    Commented Nov 10, 2022 at 17:47
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    Which ambiguity are you talking about here? As @Keelan says, the semantic ambiguity (who was in the room?) is not resolved by turning it into a wh-question. The syntactic ambiguity (is in the room part of a noun phrase the man in the room, a complement to the verb, or an adjunct?) is resolved by turning it into a wh-question, but if that’s what you’re asking about, why mention the different semantic interpretations at all?
    – Janus Bahs Jacquet
    Commented Nov 11, 2022 at 0:05

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You can't extract a prepositional object from inside a noun phrase. (It's an "island".)

I met a man from Chicago.
*From which city did you meet a man?

So if you extract the "which", then it must not have been inside the noun phrase: it must be attached to "see", not to "man".

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    This is undoubtedly true syntactically, but the ambiguity is semantic, so I’m not convinced it really answers the question. Even disqualifying any reading that has the PP as part of any NP, the PP still modifies a NP, and it is unclear which one (subject or object). But as noted in the comments, the premise of the question is false: this ambiguity is not actually resolved by turning it into a question. If I’m in the kitchen and the man is in the hall, I can answer the question “In which room did you see the man?” with either the kitchen or the hall – both make sense.
    – Janus Bahs Jacquet
    Commented Nov 10, 2022 at 17:15
  • @JanusBahsJacquet Given the wording of the question, I figure they're asking about the syntactic ambiguity specifically: about whether the PP is attached to the NP or the VP. Since otherwise, as you point out, the question doesn't work.
    – Draconis ♦
    Commented Nov 10, 2022 at 17:17
  • Hmm, I read it the other way around. One possible syntactic structure (PP inside NP) is not semantically ambiguous, but the other (PP outside NP) is, so listing both semantic options to me precludes it being about the syntax. But then of course the fact that the semantic ambiguity isn’t resolved by the question equally precludes it being about the semantic ambiguity. Perhaps it’s about a third ambiguity that I just haven’t discovered…
    – Janus Bahs Jacquet
    Commented Nov 10, 2022 at 17:48
  • I think the sentence is, syntactically, (at least) triply ambiguous. The PP could be a modifier within the NP, it could be a complement of the verb see, it could be an adjunct within the clause.
    – Araucaria - him
    Commented Nov 10, 2022 at 18:06
  • Thank you sooo much! But I have one more question. What type of island is it? I suppose it's a noun-complement island, but I'm not sure about it....
    – Agent Chuobao
    Commented Nov 18, 2022 at 13:21

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