If "he" and "Tom" are different people, then yes, 2 and 3 mean 1, and 5 and 6 mean 4.
3and 6 are a bit awkward, but they will work.
1. While he was playing the guitar, Tom entered the room.
2. While he played the guitar, Tom entered the room.
3. While he was playing the guitar, Tom was entering the room.
(Are they all correct? What is the difference between #2 and #3?)
4. When he was playing the guitar, Tom entered the room.
5. When he played the guitar, Tom entered the room.
6. When he was playing the guitar, Tom was entering the room.
(What about these sentences? Can we use 'when' instead of 'while'? Is there no difference between them?)
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