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Exercising through the Circles (4th/5ths)/Enharmonics

I've been doing it for years and I must admit I really only paid attention to the root notes. But now that I am retired, and have much more time on my hands, I have begun to pay attention to each of the notes I play. That's when I noticed I was encountering some spelling issues. And, of course, the majority of these issues deal with enharmonics. As an example, running the natural minor scales using the Circle of 4ths. One of the scales would be a Db minor. It took me a moment to realize that the relative major was an Fb Major. I then said to myself, "Dummy," this is simply the E Major/C# minor relatives.

Just a couple of questions to reinforce my understanding.

1. This is one of those situations that is theoretically correct but not used in practical application. Am I correct in thinking about it in these terms or is there more that I need to understand?

2. For those of you who teach, how do you approach this with students? Both, the running of exercises in the Circles of 4ths/5ths and also the theory behind enharmonics.
 
While there are theoretically a large number of possible enharmonic spellings, in practice, there are 15 key signatures that are commonly encountered: 7 sharp keys (from Gmaj/Emin with 1 sharp to C#maj/A#min with 7 sharps), 7 flat keys (from Fmaj/Dmin with 1 flat to Cbmaj/Abmin with 7 flats), plus of course Cmaj/Amin that has no sharps or flats, for a total of 15.

Your hypothetical key of Db minor "exists" and is a perfectly logical construction, however it is not that commonly encountered in practice, because it has 8 flats and therefore requires a double-flat (Bbb). Therefore, unless there is some compelling music-theory reason to specifically write it as Db minor, it would be more common to use the key signature of C# minor (4 sharps).
 
By the way, slight tangent, here is my answer to anyone who asks, "Why would you ever use enharmonics like B# or E#? Wouldn't it be easier to write C or F?"

In this example, you need B# so that you can play G# dominant 7, which is the "five" chord in C# minor. It shows up here (in first inversion, with the 3rd B# in the bass) as early as measure 3. Definitely watch out for the F##'s (double sharp, notated with a sort of 'x' symbol) beginning in measure 11. And if you listen through to the end, you will hear a really pretty use of E# (enharmonic to F natural). I love this kind of music. There's something almost "metal" or "prog" about its relentless commitment to developing a musical idea over 9 minutes. :)

 
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