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Helpful answers
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Mar 23, 2016 6:03 PM in response to philand57by Kenichi Watanabe,Sounds like your iPod has several separate problems. If you have not already, do a Reset (restart) on the iPod.
Learn how to reset your iPod - Apple Support
If that does not help, for the headphones problem, try different headphones to rule out faulty headphones as the cause. If the headphones jack still does not work, it is may be worn out or damaged.
For the charging issue (and connection to iTunes), try a different USB docking cable to rule faulty docking cable as the cause. If the problem recurs with different cable, the iPod's dock connector may be faulty. Charging can be done with different "pins" on dock connector. If the dock uses FireWire charging, those pins may be connecting and working. When you connect it to your computer, it uses USB charging which may not be connecting. The data connection uses a different set of pins, and those may not be connecting.
In case these problems are caused by data corruption on the iPod, you can try doing a Restore on the iPod using iTunes. This erases the iPod, reinstalls its software, and sets it to default settings.
If the problems recur after the Restore, the causes are likely to be related to hardware problems.