You can't move items up in the alias if the NameMapping does not correspond... if I have MyApp -> MyPanel -> Button1 and MyApp2 -> MyPanel -> Button2, I cannot move button 2 to MyApp because it is not in the hierarchy.
I suspect that, in your example, one of two things is the problem... either there already exists a child item off of ToolBar with the same name or mapping criteria so it is preventing you from putting them on the same level to avoid ambiguous or duplicate mappings... Or, your mapping is not necessarily the same between the two components. I'd double check the NameMapping hierarchy and make sure the relationship exists there properly.
As for "learning", in NameMapping, if you right click on an item already mapped (like your application), and select "Map Child Objects", it will map all child objects off there... it won't recursively drill down, but you can map upward from a lower level.