My hard drive crashed without me having backed up my music

I still have the music on my iPod, and the songs I had purchased transfered back onto my computer from the iPod. Unfortunately, all of the music I had downloaded from my CD collection will not transfer back onto iTunes. When I try to sync my iPod with new songs I had purchased since I bought a new hard drive, the two will not sync. Therefore I am unable to listen to new songs I have purchased on my iPod. Is there anything I can do to get the music back into iTunes from my iPod, and how can I get the two synced once more?

*Unfortunately, all of the music I had downloaded from my CD collection will not transfer back onto iTunes.*
The transfer of content from 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 music files and playlists from your iPod. I use Senuti but have a look at the web pages and documentation for the others too, you'll find that they have varying degrees of functionality and some will transfer movies, videos, photos and games as well. This is just a small selection of what's available, you can read reviews and comparisons of some of them here:
Wired News - Rescue Your Stranded Tunes
Comparison of iPod managers
Senuti Mac Only
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
Music Rescue Mac & Windows
iPod Music Liberator Mac & Windows
iGadget Mac & Windows (iPhone and iPod Touch compatible)
Floola Mac & Windows
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
*When I try to sync my iPod with new songs I had purchased since I bought a new hard drive, the two will not sync*
Once you have recovered everything from the iPod and you are happy with the content of iTunes, if the iPod still won't sync then try restoring it. Restoring will erase the iPod's hard drive, reload the software and put it back to default settings. Once the restore is complete follow the on screen instructions to name the iPod and automatically sync your songs and videos onto the fresh installation. Press Done and the iPod will appear in iTunes and start to sync. If you want to sync using selected playlists uncheck the box beside the sync automatically instruction and press Done, it will default to manual mode and you can choose whatever setting you like: Restoring iPod to factory settings with iTunes 7

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I just spoke with a friend who like you is into Apple and he just walked me through the Cloud. At least I was able to get those songs back.
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1). Connect your iPod to your computer. If it is set to sync 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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Alternatively open iTunes first and go to Edit>Preferences>Devices and check the box "Disable automatic syncing for iPhones and iPods" and choose Ok. Then connect your iPod.
3). Once you are connected and your iPod is safely in manual mode there are a few things you can do to restore your iTunes from the iPod. iTunes will only let you copy your iTunes Store purchases directly from an iPod to the computer, you'll find details in this article: Copying iTunes Store purchases from your iPod or iPhone to a computer
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Check out the instructions/suggestions here.
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There's also another method. I've successfully tested this across several different Windows PCs.
Open iTunes and select edit/preferences/advanced/general. Put a check mark in the box marked "copy files to iTunes music folder when adding to library" and also "keep iTunes music folder organized", then click 'ok'.
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You buy one and only one download of music and vids. It is your responsibility to move/copy/backup your purchases.
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My hard drive crashed without me having backed up my music

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