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In a sentence that requires the use of "that" instead of "which," can "which" still be used when followed by a preposition.

Original: "I have the photo that Seinfeld signed." Using preposition: "I have the photo on which Seinfeld wrote his name."

I understand that the latter is correct, but I'm curious as to why it is correct. Does anyone have a deeper analysis about why it sounds weird to say "on that Seinfeld wrote his name," beyond just the fact it sounds weird. I'm looking for an actual grammatical explanation because I work with technical writers who flip around the above options often and I would like to know more about the mechanics of why this works.

Edwin Ashworth
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rarach
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  • Why do you think your sentence requires "that"? – BillJ Aug 03 '17 at 14:14
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    I don't necessarily think it's a duplicate; if the chosen answer is correct, that and which are entirely interchangeable (which is a plausible answer to "when to use" them), but this OP has identified a situation where they definitely aren't interchangeable, and wants to know why. Even if one of the other answers might give a clue about this question, it would be worthwhile to have the information as an answer to a specific question (like this one) rather than the more general question asked at the proposed duplicate. @rarach, maybe you could edit your question to be more focused? – 1006a Aug 03 '17 at 15:05
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    This is certainly a duplicate. Questions, not a raft of wonderful answers, determine duplicates. However, the correct answers (which indicate that OP here seems to be under a false impression about where 'which' may be used [see their first two sentences]) are given at the duplicate mentioned; the non-availability of "I have the photo on that Seinfeld wrote his name." is brought out in Brett Reynold's answer. – Edwin Ashworth Aug 03 '17 at 15:34
  • 'I have the photo that Seinfeld signed.' and 'I have the photo which Seinfeld signed.' are exact paraphrases using a restrictive aka defining relative clause. Either 'that' or 'which' may be used in this case. 'I have the photo, which Seinfeld signed.' (note the comma) is different in meaning, using a non-restrictive relative clause. // When a preposition is fronted in the relative construction, only 'whom' and 'which' (never 'that' and arguably never 'who') may be used. 'The girl to whom you spoke...' / 'The spanner with which I unscrewed ... '. – Edwin Ashworth Aug 03 '17 at 15:37
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    Pied-piping does not apply to that, only to wh-words. The proposed "using preposition" sentence is pied-piped. Hence it can't have that. The OP's problem is that they believe the zombie rule and think this is a special exception to it. That's not a question that can be answered, – John Lawler Aug 03 '17 at 15:52
  • Just as you would not switch that and which in "That Girl" or "Which Witch? your "on that Seinfeld wrote his name" uses that to replace which in a different use of which other than the one where they sub for each other. – Yosef Baskin Aug 04 '17 at 05:11

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