Why does iTunes freeze up everytime I try to change the options?

I'm trying to change the options on my iTunes (where it says Manage music manually and Sync checked songs). Everytime I click them and go to sync it, iTunes gets a Not Responding heading..why?
I'm trying to see why songs I buy wont transfer to my iPod Nano (6) even after syncing successfully..if anyone knows another thing to try, please tell me

Hi anthonyp49046720,
I am so sorry that you are experiencing this issue & will try my best to help you with this.
Please let me know the following details :-
1) Version of Adobe Acrobat that you are using.
2) Operation System installed on your computer.
3) Are you experiencing this issue while editing a particular PDF file or you are experiencing this issue on all PDF files?
4) And, are other features working perfectly on your Adobe Acrobat?
Regards,
Aadesh

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