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I think it might be hard to queue the ipod BUT if you just let the ipod run you could get a cheap headphone extension. If you cut the extension in half you can kindof pull apart the wires inside it. If you strip off some of the insulation and then connect them loosely you can see which one turns off the headphones when disconnected. Wire that one through the switch. Then put the extension in line between the ipod and your speakers and put the switch wherever you want and you are good to go.