I recently discovered that if is considered a preposition in contemporary grammar. Is "when" considered a preposition as well? And in the following sentence, is the chunk introduced by when considered an adjunct, or as integral in that it provides the referent for "it"?

I like it when you say "indubitably".

  • The same modern grammar classifies "when" as a preposition. In your example, the PP when you say "indubitably" has a paraphrase containing noun + integrated relative: I like it on those occasions when you say "indubitably".
    – BillJ
    Nov 26, 2023 at 13:18
  • In object extraposition the "it" is a dummy element serving the syntactic purpose of filling the object position; the extraposed element doesn’t give the meaning (reference) of "it" but serves simply as a semantic argument of the VP. Btw, extraposition of PPs is controversial. Some grammars say that PPs cannot be extraposed.
    – BillJ
    Nov 26, 2023 at 13:35
  • @BillJ I wasn't aware of the controversy but that was indeed the question that came into my mind. Thank you for your answer.
    – TimR
    Nov 26, 2023 at 13:41
  • On reflection, although your example does bear some resemblance to extraposition inasmuch as what I like is your saying "indubitably", it differs from extraposition in that the final element is not a content clause, not a potential replacement for "it".
    – BillJ
    Nov 26, 2023 at 14:10
  • For the avoidance of doubt, what I'm saying is that your example does not in fact contain extraposition.
    – BillJ
    Nov 26, 2023 at 14:31

1 Answer 1



This depends on the framework. It's definitely not universally considered a preposition even in modern model-theoretic syntax (Sag, Wasow, Bender 2003, Borsley 2019). But the conditional if is indeed taken to be a preposition in CGEL (2002), a major descriptive grammar.

There are two other if's in the English language: the interrogative subordinator and a more exotic irrealis subordinator (Pullum 1988, Rocchi 2010):

(1) I wonder if it's true.if as an interrogative subordinator

(2) Imagine if it were true!if as an irrealis subordinator


When is exclusively a preposition in CGEL, although a problematic one, because it forms two subtly different constructions: fused relative preposition phrases (similar to most uses of where) and regular PPs with when as the head and a content clause as a complement (similar to the conditional if, as well as since, because and although). Both constructions function as adjuncts in the following examples:

(3) When they come, call Jane.when they come if a fused PP

(4) When they weren’t home at six o’clock, I began to get worried.when is a preposition taking a content clause complement; example due to Huddleston & Pullum 2002 (p. 1078)

But as Rocchi 2010 (p. 46) shows (Pullum & Reynolds 2013 concur), when, just like if, might have become a subordinator as well. They use an example similar to yours:

(5) I hate (it) when people say that learning Latin teaches you to be logical.

This construction is closely related to the irrealis if both semantically and grammatically. The when-phrase here is not an adjunct, but a complement, similar to phrases with if in (1) and (2). For example, like the "third if" and unlike regular when-adjuncts, it resists preposing:

(6) *When people say that learning Latin teaches you to be logical, I hate.

Irrealis if tends to occur in extraposed clauses, but with this when, extraposition is not necessary: you can remove it, and the sentence is still grammatical.

Pullum and Reynolds give some more examples of what they believe is the new subordinator when, featuring verbs like love, hate, like and regret.

Borsley, Robert D. 2019. Phrase structure. In The Oxford Handbook of English Grammar

Huddleston, Rodney & Geoffrey K. Pullum et al. 2002. The Cambridge Grammar of the English Language

Rocchi, Manuela. 2010. A third if?

Pullum, Geoffrey K. 1988. Implications of English extraposed irrealis clauses

Pullum, Geoffrey K. & Brett Reynolds. 2013. New members of 'closed classes' in English

Sag, Ivan A., Thomas Wasow & Emily M. Bender. Syntactic Theory: A Formal Introduction

  • Thanks. How about "Go right ahead. See if I care!" ? How would that if be categorized?
    – TimR
    Nov 26, 2023 at 19:19
  • @TimR That's just an interrogative subordinator. Nov 26, 2023 at 20:14
  • That's good. Just looking for familiar terra firma :-)
    – TimR
    Nov 27, 2023 at 12:45

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