Learn English – Punctuating a question followed by a further comment in a sentence: position of question mark

question mark

I am always confused regarding the accepted placement of the question mark when there is a comment or the like following the actual question in a sentence.
Consider the following options:

Shall I direct the request to you?, in which case I will proceed with
sending the email.

or

Shall I direct the request to you, in which case I will proceed with
sending the email?

Which one (if either) is correct? Is there a better option?

Best Answer

You should not combine a question and a statement together into a complex sentence.

The sentence in the question could be correctly rephrased like this:

Shall I direct the response to you and proceed with sending the email?

And, as others have pointed out, it would be correct to split it into two sentences like this:

Shall I direct the response to you? If so, I will proceed with sending the email.

But phrasing it like you do in the question is wrong. A case is not defined by asking the question in the first clause, so the "in which case" qualifier is not recognizable in the second clause. Further, the subject between both clauses is the same, so there's no reason to use two clauses. Lastly, there is no reason to combine a statement and a question together in a single sentence like this. It's never right. Don't do it.