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1 What do you think the reasons to not buy a car Jack has?

2 What do you think the reasons to not buy a car are (which) Jack has?

3 What do you think the reasons to not buy a car Jack has are?

The sentences are awkward but are they grammatically wrong?

More natural

4 What do you think the reasons for Jack to not buy a car are?

5 What do you think the reasons are for Jack to not buy a car?

Which ones are grammatically wrong?

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  • Some of these are grammatically wrong, some are just awkward, and some are better. There are some not shown that would be even better. It would help if you edited to show what suspicions you already have about the actual mistakes. Commented Dec 5, 2023 at 15:46
  • In my opinion all of them are grammatically correct.
    – user1425
    Commented Dec 5, 2023 at 15:47
  • Putting the 'Jack has' part at the end makes it ambiguous as to whether it refers to the reasons or the car (someone else could be considering buying a car from Jack). Commented Dec 5, 2023 at 15:56
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    Your opinion is mistaken. #1 is definitely ungrammatical, because it lacks an "active" verb (are in #2 and #3, which are both "technically valid" but idiomatically awful! :) Commented Dec 5, 2023 at 16:14
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    Grammatical or not, (3) is clumsy and difficult to follow. Commented Dec 5, 2023 at 17:05

2 Answers 2

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Sometimes, with questions and inverted sentences and lots of phrases, it helps to "build the sentence back up" from something simpler.

  • What does Jack have?
  • What reasons does Jack have?
  • What reasons do you think Jack has?

These are all pretty straightforward. The only thing left is to figure out the best place to stick "not buy a car." Personally, I like this:

  • What reasons not to buy a car does Jack have?
  • What reasons do you think Jack has not to buy a car?

Notice, I've gone with "not to buy" rather than "to not buy." I'm not sure why; maybe someone else can explain. Maybe it has something to do with splitting infinitives, or with the fact that we're talking about "not doing" rather than doing something. I don't personally think "to not buy" would be wrong, I just chose the other.

Now, we could also add the "not buy" phrase after "reasons":

  • What reasons not to buy a car do you think Jack has?

This is also grammatically correct and natural enough, though I would choose the previous option (maybe because it gets the focus onto Jack sooner in the sentence?). Now at this point, some of the examples you gave that are wrong get confused because they add another verb, "are." Since we have here two working options, there's no reason really to make this already complex sentence any more complicated. So your options 4 and 5 are grammatically correct, and not unnatural, but less desirable since there's a simpler option. Meanwhile, options 2 and 3 are even more inverted, to the point that they are only "technically" correct and are not only unnatural but confusing.

Finally, option 1 is just plain wrong. Let's mess with inversion of a simpler sentence:

  • What stuff does he have? <- OK
  • What stuff do you think he has? <- Also OK. Notice the subject of the sentence is no longer "he" but "you." This is an inversion of "You think he has what stuff."
  • What do you think he has? <- OK. We omitted the word "stuff"; "what" is taking its place here, working as a sort of object of "has": "he has what."
  • What do you think stuff he has? <- Not OK. Since we said "what stuff," we can't split that phrase up.

That's the underlying problem in #1. Since there's no "are," the closest correct equivalent would put "what reasons" together (and omit "the"). That would give us my second suggestion above:

  • What reasons not to buy a car do you think Jack has?

EDIT: Several comments on this answer give variations that involve "reasons are" instead of "Jack has." These are even more straightforward and are good choices, with several options for syntax:

  • What do you think are Jack's reasons for not buying a car?
  • What do you think Jack's reasons are for not buying a car?
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    Yes, I like the build-back-up method myself. One which is often overlooked in tomes like CGEL. [haha] I would add, though, "What reasons does Jack have for not buying a car?" Cheers.
    – Lambie
    Commented Dec 5, 2023 at 16:06
  • I'd get the preliminaries out of the way first: What [do you think] are Jack's reasons for not buying a car? That's still perfectly natural if we remove redundant do you think, but if you discard that from your version, you end up with What reasons not to buy a car Jack has? That's still pretty weird even if we "invert" the subject/verb being queried - What reasons not to buy a car has Jack? is decidedly "stylized". Commented Dec 5, 2023 at 16:24
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    In my neck of the woods we'd ask What do you think Jack's reasons are for not buying a car? Commented Dec 5, 2023 at 16:28
  • @TimRonsomedevice: It's all a matter of personal preference, but I'm surprised anyone would be consciously aware that most speakers in their area consistently choose to use a format that requires "reversing the inversion" to move the active verb (are in yours, has in Andy's) to before the subject (your reasons, Andy's Jack). I don't really even know what I'd say myself! I just said that's what I'd do here because my suggestion best matches OP's title, and his "more natural" versions (just move are forward to the right place). Commented Dec 5, 2023 at 16:41
  • @FumbleFingers It would be very unnatural in my dialect of AmE to avoid "Jack's reasons for X" and say in its place "reasons [for X] that Jack has" Commented Dec 5, 2023 at 19:20
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None of the proposed sentences are idiomatic. They are all awkward and unnecessarily verbose. That doesn't mean the OP's sentences are incomprehensible or so nonsensical that a native speaker wouldn't understand, I'm sure everyone reading the question understood, but the OP is making a simple concept–why Jack doesn't want to buy a car–more complicated than it should be.
Start with:

WHAT + OBJECT + AUXILIARY + SUBJECT + VERB
What movie did Jack go to see yesterday

INDIRECT QUESTION
Do you know what movie Jack went to see yesterday?

DIRECT QUESTION
What time did the movie start?

INDIRECT QUESTION
Could you tell me what time the movie started?

  1. What reasons does Jack have for not buying a car? (DIRECT)
  2. What reasons do you think Jack has for not buying a car? (INDIRECT)

WHAT [do you think]+ AUXILIARY + NOUN PHRASE + SUBORDINATE CLAUSE

  1. What do you think are the reasons [that] Jack doesn't buy a car? (DIRECT)
  2. What do you think are Jack's reasons for not buying a car? (DIRECT)
  3. Would you mind telling me Jack's reasons for not buying a car. (INDIRECT)

But by far the simplest is:

  1. Why do you think Jack doesn't want to buy a car?

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