Not all songs transferred from iTunes to iPod

iPod touch 3G, intel iMac (Leopard).
The iTunes library has just been rebuilt with all files present and correct, cover art etc and AFAIK all tunes play OK. (Took ages, but it's all good!)
1. Removed all songs from iPod
2. Updated OS to 5.0.1
3. Synced all music to iPod from iTunes. At the start I got a message saying that "This computer is not authorised to play some songs and they will not be transferred". However the iMac is of course authorised, and all the songs were either bought through iTunes on the iPod and transferred (over the last 2 years) or bought direct to the iMac, or ripped from personal CDs.
4. Unchecked "sync all songs", switched to "manually manage music" and put them on manually. Same result but without the above message apperaing.
There's 7503 songs on iTunes and only 7431 on the iPod.
Two questions:
Does anyone know why this should be?
Is there an easy way of finding out which songs are missing? I've checked the ones I remember purchasing on the iPod originally, and they're all there.

You go to iTunes>file>move folder 2 library then you slect the folder your songs that you downloaded r in and click ok.
And more you can follow this tutorial about how to tranfer music from computer to iPod.
Cheer.

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