Some songs no longer exist on ipod, but do on itunes

Hello,
I don't know when it started (maybe 6 months), but my iPod doesn't syncronize as well as before. Now, some songs that I could see and listen before no longer exist. Of course, they still appear on iTunes. My albums are incomplete. I've tried to restore my iPod by using the option on iTunes, but unfortunately did not work.
I do not what I can do. I do need help.

Are these songs purchased from the iTunes store, or from your own cds?
Been through these?
The Five Rs.

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