door of which car/which car's door

Vladv1

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1. Which car's door did you paint?

2. The door of which car did you paint?

Which is correct?
 
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1. Which car's door did you paint?

2. The door of which car did you paint?

Which is correct?
(1) definitely works. I find (2) ungrammatical and think it needs to be changed to one of these, in order of awkwardness:

(2a) Which car did you paint the door of?​
(2b) Of which car did you paint the door?​
Is (2) intended to be an in-situ (or echo) question with strong stress on WHICH? If so, I recommend revising to this:

(2c) You painted the door of WHICH car?​
 
(2a) Which car did you paint the door of?
(2b) Of which car did you paint the door?​
I agree that (2a) is more natural than (2), but I don't see what makes (2) ungrammaical.
 
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I agree that (2a) is more natural that (2), but I don't see what makes (2) ungrammaical.
I suppose it would be grammatical as an in-situ (or echo) question in a really special sort of syntactic context, viz.:

A: I painted the door of that car.
B: [I'm sorry.] The door of WHICH car did you paint?

Of course, in that case, I'd prefer this instead:

The door of WHICH car did you say you painted?
How can (2) be grammatical as a root question? Have you ever heard a root question with extended Pied Piping, that is, Pied Piping that extends beyond the preposition in a prepositional phrase to the noun above? I grant it works in relative clauses:

This is the car the door of which you painted.
[= This is the car of which you painted the door. / This is the car whose door you painted.]​

But have you ever encountered that sort of thing in a root question like (2), used by a well-spoken native speaker? I don't think I have. That is, it seems to have no "sibling sentences" -- root questions formed after the same pattern. Meanwhile, (2) sounds terrible to me. That's a full explanation of why I used the term "ungrammatical" rather than merely "not very natural" or "unnatural." The pattern it exemplifies seems, in my judgment, not to exist at all in natural native English.
 
What do you mean by root-question?
 
What do you mean by root-question?
Root questions are questions which contain inversion and which are neither embedded (I wonder what time it is) nor in situ (You brought WHICH dog?). Root constituent questions generally begin with a wh-word (Which dog did you bring?) and root yes-no questions with an auxiliary verb (Did you bring that dog? / Was the dog barking? / Have you seen my dog?). Occasionally, however, with root constituent questions, we have Pied Piping. Thus, instead of Which dog did his cat bite the tail of?, we can have Of which dog did his cat bite the tail? What I personally don't think we native speakers ever see or hear (among other native speakers) or utter in our right minds is a sentence like this: *The tail of which dog did his cat bite?
 
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NOT A TEACHER
------------

To my non-teacherly eye, it feels odd to see the object (door) before the interrogative pronoun (which).

For this reason, I prefer Annabel Lee's "Which car did you paint the door of?" over the OP's "The door of which car did you paint?" as a standalone question.

However, I could imagine a dialogue between a dissatisfied shopowner and their wise-guy employee after the former notices that the latter painted the wrong car door. The stressed part is in bold.

A: Which car did you paint?!
B: I didn't paint the whole car. I only painted the door.
A: Which car did you paint the door of?

At the same time, I could imagine the OP's "The door of which car did you paint?" used in a similar exchange:

A: Which car did you paint?!
B: I didn't paint the whole car. I only painted the door.
A: The door of which car did you paint?

I can also imagine A's response from the second dialogue being used in a different situation, with a different part stressed.

A: What did you do?!
B: I painted the door of the car, as you asked.
A: The door of which car did you paint?

I would say "Which car did you paint the door of?" is clearly the best option, especially as a standalone question, but "The door of which car did you paint?" is also possible with sufficient context.
 
Nice discussion, Glizdka. I've had a change of heart regarding the construction of (2). It does seem to be a grammatically viable fringe construction, at least in spoken English, when the context of discourse provides abundantly for presuppositions. For example, if I knew that "they" had moved to the capitol of a some state but could not remember which state, and had reason to believe that my interlocutor knew, I could see myself using the following in spoken English:

The capitol of which state did they move to?
 
Nice discussion, Glizdka. I've had a change of heart regarding the construction of (2). It does seem to be a grammatically viable fringe construction,
In other words, it is not ungrammatical.
 
In other words, it is not ungrammatical.
I suppose not, though I should be extremely surprised to find a formal endorsement of it in any comprehensive grammar.
 
I should point out that “Which car did you paint the door of?” would likely be the expected answer in a hypothetical textbook exercise designed to test whether a learner can construct questions of this type, especially since this forum is frequently visited by learners seeking advice to improve their grades.

However, I agree with 5jj that “The door of which car did you paint?” is not ungrammatical, as my views are more descriptivist than prescriptivist.
 
This is the music that the love of helped me to survive.
 
"This is the music love of which helped me surivive". Does it sound good?
It would sound much better with "my" or "the" before "love," "to" before "survive," and "survive" spelled properly:

This is the music my love of which helped me to survive.
This is the music the love of which helped me to survive.

"Love of the music" refers to anyone's love of it. How could others' love of the music help you to survive? Although the same point could be made about "the love of the music," I prefer "the" to no determiner there because "music love" can look initially like a compound, before one gets to "of which" and is forced to reparse it.
 
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It would sound much better with "my" or "the" before "love," "to" before "survive," and "survive" spelled properly:

This is the music my love of which helped me to survive.
This is the music the love of which helped me to survive.

"Love of the music" refers to anyone's love of it. How could others' love of the music help you to survive? Although the same point could be made about "the love of the music," I prefer "the" to no determiner there because "music love" can look initially like a compound, before one gets to "of which" and is forced to reparse it.
This is the music the love of which helped me to survive. Could you please explain the use of the article THE before "love"?
 
Root questions are questions which contain inversion and which are neither embedded (I wonder what time it is) nor in situ (You brought WHICH dog?). Root constituent questions generally begin with a wh-word (Which dog did you bring?) and root yes-no questions with an auxiliary verb (Did you bring that dog? / Was the dog barking? / Have you seen my dog?). Occasionally, however, with root constituent questions, we have Pied Piping. Thus, instead of Which dog did his cat bite the tail of?, we can have Of which dog did his cat bite the tail? What I personally don't think we native speakers ever see or hear (among other native speakers) or utter in our right minds is a sentence like this: *The tail of which dog did his cat bite?
So we can say "Which car did you fix the engine of?"
 
This is the music the love of which helped me to survive. Could you please explain the use of the article THE before "love"?
If, by asking about "the use," you mean to ask about the contribution to meaning that the makes in the phrase the love of music, I would say (knowing full well that it is a very tricky question and that I may be about to entangle myself in a debate) that the represents love of music as actually existent in the contextual domain picked out by the sentence in which the phrase appears, whether that domain is past, present, or future, and whether the context is nonfiction or fiction: May the love of music grow and grow! (Please note, however, that I am NOT saying that May love of music grow and grow would be incorrect.) In contrast, love of music may be used independly of its actual existence in the contextual domain: Love of music is not something everyone has/had/will have. That sentence would, in my opinion, sound weird with the.
So we can say "Which car did you fix the engine of?"
Yes.
 

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