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...or like our young student, they have what is called a mental calendar from which they can pull details about almost any date.

(The source: https://youtu.be/43JDG0E5k4U?t=212)

Could the "from which" be separated and used like this,

...or like our young student, they have what is called a mental calendar which they can pull details from about almost any date.

?

If it could, does the whole sentence sound as good as the original sentence? How could we tell if a [preposition + which] is separable? Does it depend on the particular preposition?

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The modified version of the sentence has a stranded preposition ("from"), that is separated from its object "which". That is a less formal style than a fronted preposition, as in "from which", but it's grammatical and understandable. It's common for such a preposition to be at the end of a sentence, like this:
"They have a mental calendar which they can pull details from."

There are cases where stranding the preposition can't be done, and cases where it has to be done.
In your example, it works either way. However, I don't think it's the best choice in that sentence, because the stranded preposition is in the middle of the sentence, right in front of another preposition ("...from about..."), and that makes the sentence just a little bit harder to read.

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  • Thank you for clarifying the downside of the modified version. But how do we know if a preposition can be stranded? Does it depend on the preposition, or the context? – Sam May 26 '20 at 12:27
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    @Sam It can depend on a number of things. The grammar book I have devotes three pages to it. There are cases when the P must be stranded, and cases when it must not, according to whether it's part of a fixed phrase, e.g., "in what way" (can't strand) or "what for" (must strand). Other syntactic factors play in, too. I suggest you do some searching on "preposition stranding". – Jack O'Flaherty May 26 '20 at 14:29
  • May I ask what is the name of the grammar book? It seems like a great book. – Sam Jun 5 '20 at 7:04
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    "A Student's Introduction to English Grammar", Huddleston & Pullum, Cambridge University Press. – Jack O'Flaherty Jun 5 '20 at 12:38
  • Thank you, Jack. – Sam Jun 6 '20 at 1:18

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