I can't delete any thing from itunes or my i phone

I updated itunes on my macbook pro and now I can't delete and music off my mac or my iphone 4, I have been trying for days now and am very frustrated!! please can anyone help
Thanks

Hi thanks for the reply,
before the update I clicked on the song I wanted to delete then using ctrl and click this brought up a drop down with delete, so you could delete that song. After updating I put a new album on my iphone 4 and it put every track on twice, so I tried the usual way and ctrl click bring up an option to play the song but no delete. Edit doesn't have delete highlighted so you can't delete that way. I have tried so many things on the phone and in itunes but I can't delete any of the doubled tracks. Do you know how I can sort this out ?
Thanks

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