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This is the intent of what I want to get across:

You are participating in a discussion with the moderators and as a moderator.

I want to emphasize in particular that he is not only speaking with the moderators, but as a moderator as well. I wrote it as follows:

You are participating in a discussion as a and with the moderators.

Is this correct? The issue is that "as a" expects "moderator" while "with the" expects "moderators". This sounded less strange than the other way:

You are participating in a discussion with the and as a moderator.

This one sounds totally wrong, in fact.

There are other cases as well. I can't think of any that arose naturally right now, so here's a contrived example:

He can choose to eat a or throw out all the hot dogs.

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    Whatever you do, "deleting" one of two instances of a noun with different pluralities will be awkward. You should go for something like You are participating in a discussion with the moderators, as one [of them]. He can choose to throw out all the hot dogs, or eat one [of them]. Sep 27, 2014 at 17:01
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    Conjunction reduction may not be your friend here. If you're gonna delete part of some recurrent noun phrase, you hafta delete the right parts. Never end a reduced constituent with an article -- articles must occur before the nouns they determine, and never end a phrase. For starts. Sep 27, 2014 at 17:06
  • @FumbleFingers I think your first example needs an 'and' in front of the 'as one'. The second could also be: He can choose to throw out and/or eat any or all of the hot dogs. But this would permit him to eat more than one, which I should imagine would be permissible.
    – WS2
    Sep 27, 2014 at 17:36
  • @WS2: Or maybe You are participating in a discussion with and pari passu the moderators. But any deletion steers pretty close to Zeugma/Syllepsis, because of the different meanings of the singular and plural in OP's example. Sep 27, 2014 at 17:52

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You can abandon parallelism as too awkward, or if you retain it, clarity comes when you minimize, simplify and harmonize prepositions, articles and other semantic baggage:

"Plato is in the ironic position of being a poet and huffing against poets."

"Basic numeracy dictates that you can't eat your hot dogs and have one too."

"You are participating in a discussion as a moderator among moderators."

MIGHT be sneaking away from parallelism in that last one--knowing the actual circumstances (e.g. are there other speakers/participants involved?) would help...

"The forum will be a sizeable political rodeo, with 24 head of statescattle, roped in by a panel of four moderators, held to their word by you as the historical-lies moderator." =]

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In your example, it's unclear to me whether the phrase "participating as a moderator" means that the person being addressed is a moderator or whether it means that the person being addressed is merely being treated as if he or she were a moderator. If the first option describes the actual situation, you can make your intentions clear with this wording:

You are participating in a discussion as one of the moderators.

If the second option describes what is really going on, you might be better served by framing the sentence along these lines:

You are participating in a discussion with the moderators, who will treat you as if you were a moderator, too.

As for your more general question about how to indicate that a phrase starting with a singular noun and another phrase starting with the plural form of that same noun are in parallel, I reiterate John Lawler's observation above that "conjunction reduction may not be your friend here."

The point of dropping duplicate words from a construction is to make the construction more compact and less tedious—not to introduce miniature puzzles that the reader has to solve to figure out what the construction would have looked like if it had been spelled out in full. The tactic of breaking off the first parallel immediately after a definite or indefinite article is very likely to throw readers—temporarily but annoyingly—for a loop.

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