Ipod is not synching new songs

I have an Ipod Nano. I recently acquired a new laptop, and got Itunes loaded with no problem. I had some songs that I had backed up on an external hard drive, and I got those loaded onto my laptop and into Itunes with no problem. I've purchased several new songs from Itunes, and I want to transfer them from my computer to my Ipod. When I plug my Ipod into the USB port, it pulls up my Itunes library, and at the top it says "Synching Ipod. Do not disconnect". So I wait...and usually when it's synching, it shows the songs at the top as they're being transferred. It doesn't do that. About 3-4 minutes go by, it says "Ipod sync complete. You may now disconnect your Ipod", I do, but then the new songs are not on my Ipod. I have the settings so that it automatically syncs the checked boxes in the checked libraries. I don't understand why I can't add any new songs! I have authorized this new computer, and tried just about every different setting.
I had another new hard drive a few months ago (I haven't had much luck w/ computers lately), and when I plugged in my Ipod that time, it just erased my library and I started all over w/ what I had backed up. But this time, even when I tell it to "erase and sync", it won't.
Please help!
Thanks!

With that set of symptoms, I'd try checking on a Windows Drive letter confusion. See the following document for troubleshooting advice on that possibility:
Windows confuses iPod with network drive or hard drive and may keep iPod from mounting or songs may seem to disappear

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Hello jamesia11,
Thank you for using Apple Support Communities.
Without additional information, you can use the following to get started to make sure you are hitting all the steps to sync your playlists.
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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 also read reviews of some of them here: Wired News - Rescue Your Stranded Tunes
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hi lucia!
links to other posts from posts dating back before the changeover to the new Discussions Server software (11-14 November) are typically broken.
this link should take you to hudgie's user tip:
hudgie: iPod cannot sync because one or more playlist …
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Ipod is not synching new songs

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