English translation:
no matter how
Structure:
どんなに + Verb[ ても ]
どんなに + いAdj[ くても ]
どんなに + Noun + でも
どんなに + なAdj + でも
For the sentence どんなに勉強しても、合格できないと思う, could どれぐらい be used synonymously?
i.e. どれぐらい勉強しても、合格できないと思う
@ulurujamman Hey! どのぐらい and どれぐらい are only used to express “approximately how much of (something exists)?” The question mark at the end is key as どの/どれぐらい can only be used when asking how much of something there is or how much of something was done. So, どれ/どのくらい勉強しましたか (About how much did you study?) would work, but not どれ/どのぐらい勉強しても… You might be thinking of どんだけ (which is abbreviated from どれだけ), which has approximately the same meaning as どんなに. Cheers!
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Couldn’t どうして be used to mean a similar thing?
For instance this example sentence:
どんなに辛くても、現実を受け入れなくちゃ。
Couldn’t it also be:
どうして辛くても、現実を受け入れなくちゃ。
Or does it just sound weird?
Since どうして means ‘why’, it would sound as unnatural as saying ‘Even if why hard it is, you have to accept reality.’ In sentences like this, where the speaker is trying to express ‘even if (A) is in however/whatever (way), (B)’, どんな works better since it has the meaning of ‘in what way’ or ‘what kind of’.
I hope this clears it up! 
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That makes sense, I got confused because of どうしても, I thought “why not break the ても away?”