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Helpful answers
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Aug 24, 2014 12:52 PM in response to learningtoloveappleby Jason L,Hi learningtoloveapple,
Welcome to Apple Support Communities.
It sounds like iTunes is unable to locate some of the media that you would like to play in iTunes and sync to your iPhone. The article linked below describes how iTunes stores media, where you might be able to find the missing media and how to prevent it from happening again.
iTunes: Finding lost media and downloads
http://support.apple.com/kb/TS1408
I hope this helps.
-Jason
