Saying on itunes file not available....and not syncing...

not syncing saying file not recognised?

The song file is not available?  That usually means iTunes is no longer able to find the song's file, where it was previously located.  The song may still be in the iTunes library, but the link to its song file is no longer valid.
For the song that has this error, are you still able to play it in iTunes?  If you happen to subscribe to iTunes Match, the songs that are synced to the iPod need to have their files located on the computer's local drive (not in iCloud only).

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