Itunes can't copy some songs to my ipod

So I keep getting a warning from itunes that it can't copy 3 songs from my library to my ipod. This is what the error says word for word.
"Some of the items in the iTunes library were not copied to the iPod because one or more errors occurred." It than lists the 3 songs that weren't transfered. The weird thing is that they songs were originally on my ipod but since I lowered the bitrate of all my songs, now they can't be on my ipod. It's weird because I've never had this issue until I changed the bitrate. And the songs that are giving me troubles are songs from different albums and different means of getting them. One was from a CD, the other from digital download and the other was from iTunes it's self. So... their good songs and I miss listening to them. What do I do?

Hello the_atm
If the songs are having issues syncing to your iPod, see if you can create a new version of the songs in either MP3 or AAC format and then sync it across again. You said one of the songs was a purchase from iTunes, try deleting the songs and then download it again if it will not convert.
iTunes: How to convert a song to a different file format
http://support.apple.com/kb/ht1550
How to delete content you've downloaded from the iTunes Store, App Store, iBooks Store, or Mac App Store
http://support.apple.com/kb/HT5772
Download past purchases
http://support.apple.com/kb/HT2519
Regards,
-Norm G.

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