cannot play purchased music on phone

Hello there.

 

I'm having this problem where withj tunes I have downloaded / purchsed appear in my iTunes library. They play in the library fine.Then I copy them onto my iPhone 5 and they appear, but with either a empty circle of dotted lines icon on the left. And they won't play.

 

I'm sure this is a common problem with an obvious solution, but I'm stumped. Any help gratefully received.

 

Ben

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