3rd generation Nano

When I try and sync my i-pod to the ticked/ selected music in my library it only takes half of it.I then get a box up saying that various music files could not be found. I do not understand why music that is on my library can no longer be located and synched accordingly.I have restored the i-pod various times and the result is always the same.

Hi pusaqall thanks for reply. I have everything in the same library but I am confused as to why all ticked music is not synching and only some of it is. The bar at the bottom of the screen showing the gig content goes up when I select all albums to be synched and then as soon as I click on apply it drops back to around 2.6 gb content ?
I have restored the i-pod a number of times but the same thing happens.

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