Would you help me?(質問)

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Jul 30, 2019 11:45 question
Are these examples correct?

Which would be the most natural?

#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?

Are those commas necessary?