My iphone 5 wont sync with my ipod nano 2nd gen

It sync bought songs but not my downloaded ones. Tryed copying and using different programs but it still wont sync.

Hi rgumpie,
Welcome to the Support Communities!
The article below may be able to help you with this issue.
Click on the link to see more details and screenshots. 
Managing content manually on iPhone, iPad, and iPod
http://support.apple.com/kb/HT1535
Cheers,
- Judy

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    Also see the links on that link for other useful informaion on your problem.
    In the future just update/reply to your original discussion rather than starting a new discussion.

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    I am trying to sync an old ipod nano (2nd generation) to my itunes on a windows pc but the itunes doesn't recognize the nano and says that it is synced with another  computer. Unfortunately, I don't have the old computer now. How do I sync this nano to itunes ?

    See Recover your iTunes library from your iPod or iOS device.
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    Hope someone can help.
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    http://support.apple.com/kb/TS1369
    Cheers,
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    - I would start with             
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    Troubleshooting issues with iTunes for Windows updates
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