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It seems that the following examples are of different grammatical status::

a. ?Mary is waiting for him upon his arrival.

b. There is a letter waiting for him upon his arrival.

c. Mary is waiting to give John a book upon his arrival.

Why is a odd but b and c okay?

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  • I think there's a different expection in what will happen after he arrives. I presume Mary will be informed when he has arrived and then seek him him out. The letter will not know and take no action. For that reason reason I would choose 'when' rather that 'upon' for sentence a.
    – Ross Murray
    Commented Dec 18, 2018 at 16:05
  • Could you provide more context for these sentences? It seems to me that they describe the scene at the moment the person arrives. Is that the intended meaning?
    – Tashus
    Commented Dec 18, 2018 at 17:56

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The phrase upon his arrival indicates that the arrival will trigger some event.

In sentence (b), John will receive the letter. In sentence (c), Mary will give him the book.

In sentence (a), though, there is no specified event. You could write:

Mary's wait will be over upon his arrival.

or:

Mary will greet him upon his arrival.

but the only way to complete sentence (a) would be something like:

Mary is waiting for him to arrive.

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