One of the biggest issues with raising or lowering the original note....and moving it any distance up or down in pitch is something called the Formant. Essentially it is the resonant peaks and valleys in the sound frequency spectrum for that note. When you move without adjusting the formant properly things will not sound right. This becomes more difficult the further from the original pitch you move.

https://www.youtube.com/watch?v=nPAINeIGxMc

http://en.wikipedia.org/wiki/Formant

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