ITunes won't sync some songs?

I got them from a youtube-mp3 site, (only because they're songs that never got popular enough to be on iTunes and stuff, so youtube-mp3 sites are the only way) but usually it works. I have youtube songs on my iPod and they work fine. The thing is, the last three songs I put in my iTunes library refuse to sync to my iPod. I have tried everything I could think of. I am not out of space, and my laptop is authorized. I have tried it multiple times and made sure all my software is updated. I only have two computers authorized including the one I'm using. I sync my iPod, and it says 'Syncing'. After that, it puts songs that I bought on my iPod onto my iTunes, but not those specific three songs to my iPod. It was two songs, but I added another one and it won't sync. Yes, all of them are checked, and I don't even have the option where it only copies checked songs and movies to my iPod anyways. I honestly have no idea what to do and I am starting to get very frustrated. If anyone knows how to fix this, please.

+It will try for about 3-5 minutes, then it give me a message about it not being able to read the disk or something to that nature. I even tried this for my iPod Shuffle and the samething occurred.+
In the course of your troubleshooting to date, have you checked through the following document?
"Disk cannot be read from or written to" when syncing iPod or "Firmware update failure" error when updating or restoring iPod

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