Trying to understand "while" and "during" grammar points

I am having the worst time trying to keep the below list straight. Can anyone help me tease these apart? I’ve re-read the descriptions but I’m still getting the reviews wrong virtually every time.

I’d especially like to know which of these are basically just synonyms of each other, and which ones contain noticeable differences in meaning.

際に
内に
中 じゅう
中 ちゅう
間に
ながら
最中に
ところに
時

“At the time of / when” (neutral time reference)

  • 時 – the most general (and common) “when/at the time”
  • 際に – more formal/official (docs and such) “on the occasion of”
  • ところに – right when / just as (often something unexpected happened)

“During / within a time span”

  • 内に – within a limit (before something changes)
  • 間に – while something is happening (window)
  • 中(ちゅう) – during an ongoing state (仕事中)
  • 最中に – right in the middle of (often interrupted)

“Entire duration / total scope”

  • 中(じゅう) – the whole period or area (一日中, 世界中)

“Simultaneous action”

  • ながら – doing A while doing B (has the same subject)
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This is SO helpful, thank you! I really appreciate you taking the time!

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