I have been having issues with syncing my iPod and would be extremely grateful if anyone could help. When I connect my iPod to the computer it shows on both the iPod and iTunes that it is syncing. However the songs that I have added a week ago still won't go on to the iPod and I have tried syncing it several items. The songs are downloaded from iTunes so I don't understand why it won't work.
Can you check if your iPod is set for syncing all music ? Attach your iPod to your computer and in the iTunes sidebar select the iPod. Click on Music and check if the setting is enabled or not. Also check if your enabled manually manage songs.
Also, check the Apple Support Article on how to manage and sync the music to your iPod.