Synchronizing Nano to iTunes library

I think that I make a basic mistake when I set up iTunes & did my transfers to my Nano.  As I currently understand things when you look at all tracks in your library on iTunes you should have a tick market besides any tracks that you wish to have put onto your ipod & once you have done this the sync function will then see that the nominated tracks are copied to your Nano when sync occurs.
All of the tracks on my Nano where put on it by selection the album or tracks & then just dragging them into the Nano.  The net result is that when looking at my library I can't tell which tracks have already been transferred, since very few tracks have the ticks.
Is there any way that the program can look at all tracks on my Nano & restore the tick in the complete library.?

You can't sync or drag your music back directly from an iPod to iTunes, the transfer of music is designed by default to be one way from iTunes to iPod. However there is a manual method of accessing the iPod's hard drive and copying songs but not playlists back to iTunes on Windows posted in this thread: MacMuse - iPod to iTunes
If you prefer something more automated then there are a number of third party utilities that you can use to retrieve the music files and playlists from your iPod, this is just a selection. Have a look at the web pages and documentation for these, they are generally quite straightforward.
iPod Access Mac and Windows Versions
YamiPod Mac and Windows Versions
PodUtil Mac and Windows Versions
iPodCopy Mac and Windows Versions
PodPlayer Windows Only
iGadget Windows Only

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