Q: Sync Problem !

Did you select it to sync?

To sync:

iTunes: Syncing media content to iOS devices and iPod

iTunes 11 for Windows: Set up syncing for iPod, iPhone, or iPad

I have been having the same problem wiht my ipod touch for months.  No matter what I do the I tunes library will not update on my ipod and my ipod shows songs and videos on it that my itunes says are not availale b/c they cant be found. 

The message means that iTunes can't find the actual music files.

Try:

Downloading past purchases from the App Store, iBookstore, and iTunes Store

iTunes: Finding lost media and downloads

The ones it seems that it says it cant find are cds of mine that I loaded on a long time ago and each time I open I tunes its a different set of songs etc that it says it cant find. Its very bizarre - which is why ive been trying to get my ipod to synch with the itunes so that it can find them again.  Ive tried reloading the songs from the CDs into itunes and that doesnt work either.

Try rebuilding your iTunes library

http://apple.stackexchange.com/questions/50299/how-to-rebuild-itunes-library-wit h-altered-file-locations-without-losing-playcou

, next would be to restore the iPod from backup.

iOS: How to back up and restore your content