ITunes won't sync all of my music to iPhone 4s

iTunes won't sync all of the music, it is skipping random songs, they still come up on the Music on the phone but cannot be played.. If anyone knows how to fix this please help.

Was this music purchased from iTunes or ripped? I have had problems in the past when I changed Apple IDs, and the content purchased through my previous account would not sync. If memory serves, I think it was an issue to do with the Mac not being authorised to access my old account. Signing in with my old account and authorising it resolved it. Not sure if this helps, but thought I would share.

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