Songs from 1G ipod won't play on 5G ipod

I recently upgraded to an 5G ipod from an 1G ipod, transferring my itunes library to the new ipod. A sizable number of tracks won't play on the new ipod. They just get skipped over. There doesn't seem to be anything exotic about the tracks, they were all ripped to AAC using itunes directly from the original CD.
For example, I've got an entire CD (Ken Burns Jazz, FWIW) where none of the tracks will play. If I try to play the entire album on the ipod the unit just skips from one track to the next, not playing any of them. They all play fine in iTunes.
I'd guess about 1/5 of my songs won't play, and so far I haven't been able to find a way to predict which tracks will or will not play, based on bit rate or any other specs.

ive had that issue, even tho i didnt transfer songs
this one time i deleted my itunes library files from my documents/mymusic by accident, and my itunes library was blank
i re added all my stuff back in, and then i plugged in ipod and like ur case, half the songs didng play. and plus, every song had the same album art. every single song that had an albumb art showed a ludacris red light district artwork.
i restored the ipod with the ipod software, and reloaded my whole library again.. took forever but it worked

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1). Connect your iPod to your computer. If it is set to update automatically you'll get a message that it is linked to a different library and asking if you want to link to this one and replace all your songs etc, press "Cancel". Pressing "Erase and Sync" will irretrievably remove all the songs from your iPod.
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3). Once you are safely connected there are a few things you can do to restore your iTunes from the iPod. There are a number of third party utilities that you can use to retrieve the music files (purchased and non purchased) and playlists from your iPod. I use Senuti but have a look at the web pages and documentation for the others too. You can read reviews and comparisons of some of them here (you'll find that they have varying degrees of functionality and some will transfer movies, videos, photos and games as well):
Wired News - Rescue Your Stranded Tunes
Comparison of iPod managers
A selection of iPod to iTunes utilities:
Senuti Mac Only (iPod Touch & iPhone compatible)
PodView Mac Only
PodWorks Mac Only
iPodDisk PPC Mac Only (experimental version available for Intel Macs)
TuneAid Mac only (iPhone and iPod Touch compatible)
iPodRip Mac & Windows
YamiPod Mac & Windows
iPod Music Liberator Mac & Windows
iGadget Mac & Windows (iPhone and iPod Touch compatible)
Floola Mac & Windows
Music Rescue Mac & Windows (iPhone and iPod Touch compatible)
iRepo Mac & Windows (iPhone and iPod Touch compatible)
iPod Access Mac & Windows (iPhone and iPod Touch compatible)
TouchCopy Mac & Windows (iPhone and iPod Touch compatible)
There's also a manual method of copying songs from your iPod to a Mac or PC. The procedure is a bit involved and won't recover playlists but if you're interested it's available on page 2 at this link: Copying Content from your iPod to your Computer - The Definitive Guide
4). Keep your iPod in manual mode until you have reloaded your iTunes and you are happy with your playlists etc then it will be safe to return it auto-sync.
5). I would also advise that you get yourself an external hard drive and back your stuff up, relying on an iPod as your sole backup is not a good idea and external drives are comparatively inexpensive these days, you can get loads of storage for a reasonable outlay: Back up your iTunes library by copying to an external hard drive

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Connect your iPod to your computer. If it is set to update automatically you'll get a message that it is linked to a different library and asking if you want to link to this one and replace all your songs etc, press "Cancel". Pressing "Erase and Sync" will irretrievably remove all the songs from your iPod. Your iPod should appear in the iTunes source list from where you can change the update setting to manual and use your iPod without the risk of accidentally erasing it. Also when using most of the utilities listed below your iPod needs to be enabled for disc use, changing to manual update will do this by default. Check the "manually manage music and videos" box in Summary then press the Apply button: Managing content manually on iPod
Once you are safely connected there are a few things you can do to restore your iTunes from the iPod. If you have any iTunes Music Store purchases the transfer of purchased content from the iPod to authorised computers was introduced with iTunes 7. You'll find details in this article: Copying iTunes Store purchases from your iPod to a computer
The transfer of content from other sources such as songs imported from CD is designed by default to be one way from iTunes to iPod. However there are a number of third party utilities that you can use to retrieve the music files and playlists from your iPod. You'll find that they have varying degrees of functionality and some will transfer movies, videos, photos, podcasts and games as well. Have a look at the web pages and documentation, this is just a small selection of what's available, they are generally quite straightforward. You can read reviews and comparisons of some of them here:
Wired News - Rescue Your Stranded Tunes
Comparison of iPod managers
TuneJack Windows Only
iPod2PC Windows Only
iGadget Windows Only
iDump Windows Only
SharePod Windows Only
iPodRip Mac & Windows
YamiPod Mac and Windows
Music Rescue Mac & Windows
iPodCopy Mac and Windows
iRepo Mac & Windows (iPhone and iPod Touch compatible)
iPod Access Mac & Windows (iPhone and iPod Touch compatible)
There's also a manual method of copying songs from your iPod to a Mac or PC. The procedure is a bit involved and won't recover playlists but if you're interested it's available on page 2 at this link: Copying Content from your iPod to your Computer - The Definitive Guide
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