Planning to use 1 arrow to hit a second target if it misses the first target


I’ve read a lot about “shooting the other enemy” and how enemies don’t occupy the entire 5ft square; however what I can’t find is the following scenario:

two orcs one arrow

I intentionally position my character to have a straight line with two enemies. I’m aiming for the first one but in case it misses I want my arrow to continue and possibly hit the next enemy. My understanding is that I can miss for 2 reasons.

  1. I shoot slightly wrong direction
  2. I shoot correctly but the enemy dodges.

It is the situation (2) that I want to take advantage of and basically roll again fo the second enemy, perhaps even with advantage since it didn’t expect to be shot. Would you allow this? What would you ask to roll?