My songs got deleted

So im not very good with all these technology stuff so please describe with full details
i was trying to download the newest version itunes and when i synced my phone with my imac since i just got it and it basically deleted like 75% of the songs i have but i have the same songs on my macbook pro and im trying to figure how to back it up. It's only letting me to back up the songs i bought from itunes and not the other ones that i either got from my friends or free. The problem is that my itunes on my macbook pro is really old its the version 10.5.2 and when i connect my phone with my laptop and click on the music section under phone it shows this
Pleas help me i am in desperate of some help. this is so frustrating.

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