Why wont my new songs transfer to my ipod

I'm trying to sync my ipod classic and itunes keeps 'not responding'

Hey Dalmel03,
If you are having an issue with your iPod classic not responding when connected to iTunes, I would suggest that you troubleshoot using the steps on this page - 
Apple - Support - iPod - iPod classic Troubleshooting Assistant
Thanks for using Apple Support Communities.
Be well,
Brett L 

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