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I was looking at the title of this post:

To whom does the Islamic State sell their oil?

and it sounds strange to me. Shouldn't the word order be the following?

Whom does the Islamic State sell their oil to?

Or are both correct? And what is the rule that dictates the correctness?

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This question relates to two debated points of English style: Who vs Whom (warning: silly but excellent explanation) and whether it is OK to end a sentence with a preposition (short answer: "yes — depending").

"Whom" is not common in informal (and American) English. Also, in informal English, you may end a sentence with a preposition. Consequentially, if you are going to use "whom", you already sound more formal and probably should not end a sentence with "to".

So a question such as

To whom are you speaking?

is natural, but formal. Most would instead say (some variation of):

Who are you speaking to?

By the same logic the natural, informal version of your example would be:

Who does the Islamic state sell their oil to?

As with many things, which you use depends on your audience. It can sound odd to be formal with friends and coworkers, but it can be similarly inappropriate to be too informal in business or professional communication.

However even this varies considerably in different parts of the world and different industries. As an American — or, more specifically, a Californian — I only use "whom" as an affectation to make me sound particularly formal (or British). Since I work in technology, there is no need for me to use it professionally, as technical communication tends to be informal. The only place I might use it is with legal documents, formal letters, or invitations to formal events.

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    Point of information: "whom sounding British" conforms to a stereotypical view of a British person (often used by people in the US) - i.e. that they are "posh" and English (rather than Scottish, Welsh or Northern Irish) and therefore speak formally. (At least in speech) It is very rare to hear anyone in Britain using whom - I would wager that most Brits wouldn't know how to use it properly! – SteveES Jun 14 '17 at 16:04
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    One of the few remaining uses of whom in British English is the salutation of a general-purpose official document: "To whom it may concern." it is hardly ever used in speech. – alephzero Jun 15 '17 at 0:37
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To whom does X sell their Y?

Who does X sell their Y to?

Those are the idiomatic choices. The second is colloquial—used in conversation. The first is formal and appears in documents of a more formal nature (corporate communications, legal documents, economics textbooks, etc).

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    Note that there's no reason why "Whom do they sell it to?" wouldn't be acceptable as well, and indeed I'm sure I've heard sentences on that model. It would just be unlikely for the higher-register "whom" to coexist with the separated preposition. – Luke Sawczak Jun 14 '17 at 13:53
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    @Luke Sawczak: Whom....to would be a mixing of registers. That is a reason why you won't hear it much, if at all. And grammatical is what peeps does. So I'd have to take issue with your statement that there's "no reason why". – Tᴚoɯɐuo Jun 14 '17 at 14:23
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    Am I shifting the post too much if I ask you to please redirect me to the rule that requires the "to" at the beginning? – Federico Jun 14 '17 at 14:40
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    @Federico It's called pied-piping. Putting the to at the end is called preposition stranding. – SteveES Jun 14 '17 at 14:56
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    @Federico - I don't think you're not shifting the post too much; however, if you had asked that in your original question, I probably would have cast an upvote. "Which of these two is correct?" questions are quite bland and ho-hum. "Why are both of these correct?" questions are more challenging and interesting. – J.R. Jun 14 '17 at 15:13
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You could also go more active and ask:

"Who is buying the Islamic State's oil?"

Switching the verb allows you to avoid starting or ending the sentence with the awkward 'to'.

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