Syncing Music from iTunes to iPad2 not working

Hello All,
I have tried searching for this in the forums, but cannot find a solution.
I have an old iPod with video 30gb, that has all my music on it, about 5800 songs. All the songs play on the iPod. They are all synced on my iTunes (latest version).
I just got the ipad2 (iOS5.01), and ran sync. I can see all my songs on the iPad, but most of them are greyed out. I cannot play those. There are a few that are not greyed out, which I can play. The iPad is set to sync all the music folders automatically.
Any ideas?
Thanks!

Sounds like a DRM (Digital Rights Management) problem. Newer iTunes music is DRM free, but anything over 5 or 6 years ago may not be.

Was all the music on the iPod purchased with the same iTunes account that you are currently using for the iPad?

If not, go to the Store menu in iTunes on the Computer and authorize your computer with that older account. Then try re-syncing.

That's my best guess.

Thanks for the response. Somehow, when I synced next, it transferred all the songs

That's good. You must have scared it.

I use this tactic all the time. When I really want to intimidate my computer I open the terminal. Who wouldn't be afraid of something called terminal?

PC users are at a disadvantage there. Command Line just sounds bossy. :D

I'm having the same sort of problem. A song i purchased from itunes, Adele's "rolling in the deep" wont sync with my ipad2 which is the device i purchased the song with. Its in my itunes, on the playlist, the playlist syncs but minus the song. I cant figure it out. Any advice?

Try turning the play list off, and sync, then on again, and sync. No other ideas without being able to look at the iTunes library and track itself.

Thanks. Didnt help as i tried that. Even made a new playlist. Still no luck. Its there. But i had to re-download the song from itunes to the ipad2 again. I'm thinking it might have something to do with the amount of devices i put it on. It started after i placed the song on my desktop. As i recall though you can put it on 5 devices. I have the song on a Nano, PSP Go, ZUNE, and only1 computer. Would my desktop be the 5th device so it wont sync back to the Ipad2? Thats a question. Now i already tried taking it off the desktop and syncing. Still wont work. But thats when it started.

Five computers can be authorized with a single iTunes account. iTunes on a computer should be able to sync with up to 10 devices. At least that's what I remember reading. I've never had enough devices to give it a test.

But since you've just placed the songs on the desktop, have you authorized that computer?

Go to the Store menu in iTunes and choose Authorize This Computer; use the same Apple ID and password that you use for that iTunes account. If you have more than one iTunes account and music from both, you'll need to authorize the computer for both.

If you ever stop using that computer with your iTunes account, don't forget to de-authorize it. It's a recoverable mistake to run out of authorizations, but best to avoid it.