Linguists have often assumed that the principles of English syntax do not allow a dependency between the head noun and the "gap" in a relative clause to span the boundaries of an adjunct such as a conditional if phrase. They will invent pairs of this sort to illustrate the ungrammatical results:
- I'm working with a man that I think you would absolutely hate.
- *I'm working with a man that if you saw you would throw up.
In the first, the meaning of the relative clause is "I think you would absolutely hate him", and syntactically there is a gap where the object of hate (underlined) would have been. But in the second, the meaning of the relative clause is if you saw him you would throw up, and the underlined pronoun is inside the conditional adjunct if you saw [him]. Having the gap inside the adjunct is not permitted, they say.
And they mean that descriptively: the claim is not that you ought to avoid sentences like 2 above; the claim is that all speakers have a natural instinctive aversion to syntactic structures of this sort.
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