Well that's an easy one. Your iPad is not a Peter Gabriel Fan. 😁 I am just kidding .....
The dotted circles next to the songs means that there is a problem - which is obvious, I know - but many times it indicates that the songs got "stuck" trying to sync to the device. They are sort caught in limbo, if you will.
Do these songs appear on the iPad at all? Greyed out perhaps? You could try unsyncing all of your music, restart your iPad and then try syncing it all back again.
You might also consider deleting the songs and downloading them again.
The "dotted circle" issue in iTunes can be caused by a number of things and it can be resolved in a number of different ways. Sometimes restoring the device is necessary. I hate to be this vague, but you can Google the problem or do a search in the ASC using the search field in the upper right corner and you will find many articles and discussions about it. Maybe something in one of those will help you resolve this.