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For example,

1.Where is it that you told me to bring home?

2.Where is it, which you told me to bring home?

("It" is not a place but an object such as bag or apple)

I think both are natural and grammatically correct because as for 1, I need to use "that" so as to specify what is "it" I'm referring to if "you" seem to be not sure what I'm indicating, but as for 2, I don't need to use "that" to specify "it" if "you" have already known well what is "it", so just to add information, "which" seems to be a better choice in this case than "that". But if they are not natural as well as grammatically wrong, though my assumption is possible, could you answer this question with your natural-sounding examples?

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    Neither is really "natural" in your context. Native speakers would usually ask Where is what you told me to bring?. Or maybe whatever [it is] [that you told me to bring], but that would tend to imply even more contempt / insouciance regarding the thing you couldn't be bothered to remember the name of.
    – FumbleFingers
    Commented Jun 17, 2019 at 18:12
  • @FumbleFingers So, isn't it grammatically possible to modify "it" with the relative pronoun, which or that?
    – GKK
    Commented Jun 17, 2019 at 18:14
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    @Floret Yes, but not in your example sentence. What is it that you told me to eat? would be fine.
    – Jason Bassford
    Commented Jun 17, 2019 at 18:16
  • @JasonBassford Isn't "that" modifying "what", not "it"?
    – GKK
    Commented Jun 17, 2019 at 18:17
  • @JasonBassford That doesn't modify it in your example.
    – user230
    Commented Jun 17, 2019 at 18:42

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This is common with what is:

What is it that you said earlier?

and where is when it is a place, but not when it is a thing.

Where is it that he talked to you?

Where is it that I bought?

Both of these sound like it is a place.

Where is what is better:

Where is what I bought?

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  • But strictly speaking, isn't "that" modifying "it", not "what" in your first sentence?
    – GKK
    Commented Jun 17, 2019 at 18:24

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