I have a 5th Gen Ipod Classic 150G. I've read there there are some issues with them and Linux. Clementine transfers my new music as files to the iPod as if it were a hard drive. I can look at the files from my computer but I cannot listen to them. How can clementine send my music so the ipod can see, read and play them?
Not sure about Clementine as I don't use it. However I believe it's based on Amarok 1.4 which IIRC did not have native ipod support.
http://www.clementine-player.org/
suggests that you can copy the files to the ipod which means the ipod should see and play them. Remeber that when you copy files to the ipod you need to hit save otherwise the ipod's database won't get updated and so the new files won't be seen. Also, you might need to install libgpod to provide the functionality you need.
In my experience If you simply want to manage your Ipod then I can confirm gtkpod is specifically designed for that purpose and works very well with my 80Gb Ipod classic. Also Amarok 2 works fine as well.
Hope this helps
Which Clementine version do you use ?
At first, you should try the latest Clementine version (1.0.1), which should support your Ipod. You can download the deb package for your Ubuntu version at:
http://code.google.com/p/clementine-player/downloads/list
or stay up to date with Clementine via PPA:
Check exactly the how big is your ipod(no such thing as 150GB ipod, 160 maybe) and the generation.
Mount the iPod (connect the cable, wait for the system to report it was mounted)
Click the devices tab in clementine, and wait for the program to recognize the iPod
Drag some music from the main list to the iPod window.
If this is what are you doing, you might also try to downgrade the firmware of the iPod( I read it is possible, this usually causes some pain)
Use floola (search for it, alothough slow, this is the software that worked for me without any issues)
Last, but not least: PRAY!!!
I had a problem quite similar, I could put my music on my iPod Classic (160Go), I could then see them on my iPod but it was impossible to listen to it. I just figured out that the music I had downloaded on my iPod were no .mp3 files, but .ogg files. That is my problem, I converted it and it is working. So beware with this, it might be your problem too. Hope it will help...