My ipod touch has stopped downloading new music (purchased via internet or from a CD) from iTunes when I sync it, how do I fix this?

I have a 32 GB ipod touch with plenty of space on it still, but when I sync it to iTunes, any music I've recently added will not download to the iPod. It was working fine until a month ago, but now even though the new songs are visible on iTunes in the "On this iPod page" but they show up as not downloaded. I've run a diagnostic test on my iPod but it said everything was working fine. Is there a way to fix this? I have purchased and downloaded music from cds and all of a sudden I can't add them to the library on my device.

What exactly happens when you try to sync?
Does iTunes see the iPod?
Was the iPod previous synced to another iTunes library/computer?
Have you successfully synced from this iTunes library/computer before?
If so have you done anything like update iTunes on the computer since it last successfully synced?
Do the songs play in iTunes?
Does any media now sync to the iPod?
Do you have the right boxes checked to sync?
iTunes: Syncing media content to iOS devices and iPod
Try syncing using the manual method
Managing content manually on iPhone, iPad, and iPod
Backup the iPod to iTunes and then restore from that backup
]iOS: Back up and restore your iOS device with iCloud or iTunes

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iTunes: Syncing media content to iOS devices and iPod
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