Error Message when Copying form Library to iPod

When I try and copy music videos from the library onto to my iPod (which originated from my computer via You Tube) some are successful whilst some are not. The message I get is :
"Some of the items in the iTunes library, including "(name of music file)" were not copied to the iPod "Administrator's iPod" because they could not be found."
What is the reason for this and how do I get all of the videos to be copied across?
By the way, I also get this same message when trying to copy across music as well so if the answer covers both problems please let me know.
I also do not know what videos and music I have in the library after bringing them over from my computer. How do I check if everything on my computer now sits inside the library prior to me using the sync command?
Grateful for anyone's help in this.
Patrick
Johannesburg SA
27.05.2014

if you see an beside the music/video then it will not play or sync. if the music/video does not exist in the location itunes has then it will not be able to find it.

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Error Message when Copying form Library to iPod

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