I can no longer add songs I have not purchased in iTunes onto my phone.

Hi,
I have an iPhone 4S and had been using it with a PC until recently, when I upgraded to a macbook pro. I have synced my phone in iTunes with the new computer and all music I purchased from iTunes can be moved off and onto my phone. Any other music I try to add onto my phone shows it is added on the computer, in iTunes, but does not go onto my phone. This is so frustrating! I just spent an hour with someone from the chat help and they couldn't help me. I have no coverage for my phone so I can't chat with anyone else. Anyone know what I could do?
Thanks so much!

Carolyn Samit, what are yo saying? He say he has a MC086LL at iOS 4,2. That is a 2G iPod. The software update comes with iOS 5 and the 2G can only go to iOS 4.2.1
For 31MToweVe
31MToweVeWhat happens when you try to sync?
Was the iPod previous synced to another iTunes library/computer?
Have you successfully synced from this iTunes library/computer before?
Do the songs play in iTunes?
Do you have the right boxes checked to sync?
iTunes: Syncing media content to iOS devices and iPod        
Try syncing using the manual method if you have not yet tried that.

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