Need to sync very old v.4 ipod nano w/new iMac running Os X.8.5

I was using my ipod nano v.4 with Tiger. When I try to use it with my new iMac I cannot see a control for syncing it. I have successfully downloaded my favorite podcasts. I can't find where to load them to the ipod. What am I missing?

I'm not sure what the "key" is, but there is a device button in the latest iTunes that is used to select the iPod.
The latest version of iTunes hides the familiar sidebar (along left side of window).  If you want iTunes to (mostly) work like the old version you used with Tiger, you just need to show the sidebar.  From the iTunes menu bar, under View, select Show Sidebar.
With the sidebar visible, the device button goes away, and you can do things like you did before.  As a long time iTunes users, I like "old school" iTunes... 

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    Follow the instructions of tt2 given in https://discussions.apple.com/thread/5822086

  • TS1474 I changed my computer (old one is dead!) and now when I want to sync the contents of my iPod onto my new computer, it tells me I can only sync with one computer (i.e. the one that died!) How do I get around this??

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    My old iPod Photo sync'd with 10.6 but won't with my new iMac running 10.7, I get an error message and a message that it could not sync, am I done?

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    how to transfer music from old iPod nano to new iPod touch ?

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    See Recover your iTunes library from your iPod or iOS device.
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    Here is how to send it to apple.
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  • TS4223 I want to copy (sync) the contents of my ipod to a new computer, how?

    I want to copy (sync) the contents of my ipod to a new computer, how?

    See Recover your iTunes library from your iPod or iOS device.
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  • I have an iphone 4S with broken wifi (!) and I need to sync my contacts before I set up my new iphone 6. I thought contacts synced automatically with itunes but seems not.  I've found my Apple address book but contacts are outdated. What to do? Help!

    I have an iphone 4S with broken wif i :-( and I need to sync my contacts before I set up my new iphone 6. I thought contacts synced automatically with itunes but seems not.  I've found my Apple address book but contacts are outdated. What to do? Help!

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  • Generation 4 iPod Connection to new iMac intel core 2 duo

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  • How do I transfer the music from my iPod to my new IMac computer (95% of the music on it is from CD's I own)?

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