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I am correcting a year-one student's homework. Verbatim, they wrote "Qui Davus interrogate Iulius to interrogate?," meaning, I believe, to ask "Whom does Davus ask Iulius to ask." I'm having difficulty finding a proper way for the question to be written such that the emphasis is still on the "whom." Regardless, the proper form is beyond the student's current level.

I've considered "Davus interrogat quem Iulius interroget" but I believe that that changes the sentence from an interrogative to a declarative.

"Davus Iulium quem interrogare interrogat?" seems awkward and inappropriate as well.

The best way I can currently think of is to put the first asker into a subordinate relative clause: "Quem interrogat Iulius, quem (ipsum) interrogat Medus?"

I'm also thinking that "interrogare" is the wrong verb for Davus; I've considere using "iubere" or "orare," but the proper syntax still eludes me.

I'd love to hear others' opinions.

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    I think your student is using Google Translate... I have an idea for this, but I have to see if it ever has been done or it's just something I think works. Essentially it's an indirect command as a direct question, and I don't know that syntax off the top of my head. It feels unnatural in Latin, but let's find out and see! Commented Mar 4 at 2:04
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    My first approach would be Quem Davus Iulium rogat, ut roget? Not entirely unambiguous, but is there anything wrong with that? Commented Mar 4 at 6:48
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    I'd start with something like quem Davus petit ut Iulius (inter)roget? Also not entirely unambiguous though. Alternatively, I'd recast as quem vult/iubet Davus a Iulio (inter)rogari? Commented Mar 5 at 1:35
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    @cnread: Why is it not just an indirect question e.g. "Davus Iulium rogat quem ille rogare debeat,"? Commented Mar 5 at 9:52
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    @Figulus edited to say Davus. Thank you for catching that. Commented Mar 7 at 13:08

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If your student is in first-year Latin I suspect she/he doesn't have the grammar necessary to do this, but the most natural way to do this seems to me to be something like Quem Davus a Julio rogat ut interroget? or maybe, if you're worried about ambiguity, ut hic interroget. I'd make Julius an indirect object just because Quem rogat ut roget is kind of ugly and also creates a lot of ambiguity and room for confusion. I've kept the same verb in both cases because that seems to be what your student is going for, but rogare with an indirect object is pretty rare and also on the whole it's not a particularly elegant construction with the repeated verb. My preference would actually be something like Quem Davus a Julio poscit ut interroget?

But as I say I suspect your student doesn't yet have all the necessary grammar.

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