I can't sync itunes on iphone; only apps, bookmarks, etc. will update

I have an iphone 4 and a fairly new laptop that my itunes was on until it recently got a virus. Since I spoke to Dell and reinstalled everything to factory settings on my computer, it doesn't sync my music, but it does sync my contacts, apps, etc. Now, I need to preface that if I buy itunes, they will sync, but I have songs that were down loaded from clip converter, etc. that the computer doesnt recognize and sync to iphone. Is this because they are not purchased from itunes? I never had this problem before my computer crashed. One question I had was do I need to have "sync music" checked off?? I am also hooked up to icloud...thanks.

same thing is happening to me they tell me to group songs into playlist of 20 and import them manually to see which songs wont sync. this is stupid for to reasons 1 ik the songs that wont update they are the recent ones and 2 i have 2420 songs in my library so it would take for ever

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