Duplicate songs and sync fail

I tried syncing my iPod Classic and accidentally created duplicates of ALL my songs. I have hundreds of songs in my iTunes library. None of the new music I purchased successfully syncing and now my iPod Classic only has a small number of songs to listen to. How can I organize my iTunes library so it only displays a song once and most importantly, how can I sync my new purchased music successfully?

Hello Shanette,
You may want to set up your iPod classic to manually manage the music. That way, you can just drag the new songs to the iPod and also search for and delete duplicates.
This box would need to be checked if you are manually managing content over to your iPod:
You can find the full article here:
Managing content manually on iPhone, iPad, and iPod
http://support.apple.com/kb/ht1535
Once you have that enabled and your iPod selected, you can use iTunes' feature of showing duplicate items so that you can see them all at once and delete the duplicates that you want to remove:
Choose File > Display Duplicates to show duplicate items (matches are based on the song name and artist). If you have multiple versions of the same song (for example, live and studio versions, or versions from different albums) you can hold the Alt or Option key (for Mac OS X) or the Shift key (for Windows) and choose File > Display Exact Duplicates. This will show only duplicate songs having the same name, artist, and album.
If you are using iTunes 11 (the latest version of iTunes at this time), you will need to go to View>Show Duplicate Items (you can hold Alt or Option here as well to get the Show Exact Duplicate Items option). You can find the full article here:
How to find and remove duplicate items in your iTunes library
http://support.apple.com/kb/ht2905
This should help you identify the duplicates all at one time so that you can delete the extra versions of songs. I hope this helps get you back on track!
Thank you for using Apple Support Communities.
Best,
Sheila M.

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