New Mac can't transfer songs from library to iPhone or iPods

I just bought a new Mac Mini because my iBook died. My iTunes library is stored on an external hard drive. I can see the library in iTunes, but when I try to move them to my iPhone or iPods I get an error message. It states that the new computer must be authorized. I do the authorization process and it tells me that this is computer of 2 of the 5 that I can authorize to play music and it is authorized. But, I can play the songs thru iTunes, but can't transfer them to any other devices.
The majority of the music in my library wasn't purchased thru iTunes. It is music ripped from purchased CD's to the hard drive and then imported into my library. I have had no problems for the last 5 years with this library on the laptop.
Any ideas on what I am doing wrong, or suggestions on how to solve the problem?
Thank you in advance for any help.
Angela

IS your ipod in Automatic mode or Manual.. Meaning if it is in manual mode you must transfer the songs manually. TO change - With ipod connected go to edit - preferences - ipod from that you ca select whether you wat automatic "yes" or manual

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