Music won't sync

I have updated itunes and iPhone software, so that is not the issue. I have several songs that stay in the 'purchased not on IPhone' on iTunes on my phone and are never synced to my music. No matter how many times I tell it to download it goes right back to the folder. On my 'recently added' playlist it has a circle that's partially colored in because it knows some songs aren't in the playlist, however when I hit the circle, it takes all the songs back to icloud and I have had to manually click every song on my phone to get it to redownload again. It won't do it automatically. No music syncs on iTunes anymore. Its as if everything is on some sort of manual mode yet I can't change it. I've tried to go on ITunes and manually sync music but the option is gone. Going insane.