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It is kind of uncommon for me to see a head noun belong to a subordinate clause or phrase of a relative clause. I don't know if the usage is wrong or correct.

So, are the examples below grammatically correct? These examples are restrictive relative clauses I came up with (I don't know whether they are correct or not).

(1) This is a car which I sold my old stuff in order to buy.

(2) Knowledge which I solved this problem with was learned in school.

(3) The technology which I sent this file via is called email.

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    They are all grammatically acceptable sentences. They are clumsy and unnatural but correct. – jwpfox Nov 28 '20 at 11:23
  • I agree with the last comment, but I don't follow your first sentence. Can you explain your concern in more detail. – BillJ Nov 28 '20 at 13:46
  • @BillJ In (1), "car" is the object of "buy", and "buy" is in a subordinate phrase (i mean the adverbial phrase "in order to") of a relative clause. This structure confused me, but according to your reply to the answer by Astralbee, (1) is a grammatically correct sentence, am I right? – vincentlin Nov 28 '20 at 17:15
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    Yes: (1) is OK. "to buy" is an embedded sub clause within the relative clause, with "which" (i,e,"car") as its object. – BillJ Nov 28 '20 at 18:08
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They are all wrong.

This is a car which that I sold my old stuff for in order to buy.

This requires the preposition "for" to indicate the purpose. You sold the stuff to buy the car.

I have corrected your use of 'which' to 'that' because you should only use 'which' in this way to introduce a non-restrictive clause. You have the same issue with your other two sentences:

The knowledge which that I solved this problem with was learned in school.

The technology which that I sent this file via is called email.

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  • In British English, however,that’ and ‘which’ can both be used for restrictive clauses, allowing for a bit more flexibility. OP's examples all look a bit clunky to my, but I have no problem with their use of which as opposed to that. Which to me is just pointless AmE pedantry that will probably fade over the coming decades. (Or That to me is just pointless AmE pedantry which will probably fade over the coming decades! :) – FumbleFingers Nov 28 '20 at 13:27
  • I prefer "that" in this case, but "which" is perfectly grammatical in both integrated and supplementary relatives. The addition of "for" in the first example would be wrong since it has no understood object (note that "car" is object of "buy", not of "for"). – BillJ Nov 28 '20 at 13:36

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