Would you help me?(質問)

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Jul 30, 2019 11:45 question
Are these examples correct?
(次の文は正しいでしょうか)

Which would be the most natural?
(どれが一番自然な言い方でしょうか)

#1 Studying in his room, he fell asleep.
#2 He fell asleep, studying in his room.
#3 Falling asleep, he studied in his room.
#4 He studied in his room, falling asleep.

Are there any differences about meanings or nuances?
(意味やニュアンスの違いはありますか)

Are those commas necessary?
(コンマは必要ですか)