Possible to optionally Trigger Context Menu Item in the Context Menu navigation sequence if it is present?

Is it possible to optionally a Trigger Context Menu Item in the Context Menu navigation sequence, if the item is present?

For example in Google Chrome, right-clicking a tab, and attempting to create a new Tab Group, will look different if there are already Tab Groups available in the same browser window vs. if there are none.

  • If there is already a Tab Group in the browser window available, the sequence for creating a new Group will be: Add tab to group > New Group

  • If there are none, the sequence will be: Add Tab to New Group

In order to handle both of these situations, the Context Menu Trigger sequence look something like:
"do (3);(1) if (1) is available, otherwise do only (3)".

NB: (3) and (1) being the nth context menu items in their respective context menu lists.

It doesn't seem to work to simply have the sequence be "(3);(1)" to trigger the first item and second item if they are available – because even if the first item is available, if the second isn't, then the first item will not trigger. Both appear to have to be present for it to work at all?