Various Electronic Devices
The propietary Apple miniplug female connector for iTouch 2G and maybe others has 5 pins. The Tip has two connections, to detect if a plug is inside. When both sides are shorted, the internal speaker is shut down. When open after shorted, the music stops (same as removing the earphones)

Pin
Name
Description
Tip Side-A Left earphone channel
Tip Side-B Plugged-in detection (if shorted with Tip Side-A)
Ring 1 Right earphone channel
Ring 2 Ground (0V)
Sleeve Microphone

I needed to change the female miniplug connector on my iPod Touch 2G, and instead of using an official propietary replacement I soldered some cables and took them out of the chassis, and added a female miniplug, and a switch to turn on and off the internal speaker.

NOTE: I'm almost completly sure about the Left/Detect sides, but this might be the other way around.
I've discovered that in my model (iTouch 2G), music always comes out of the channels, even if the "plugged-in" detector is open. In this case both the internal speaker and external earphones do play music. So, you might try to test this before deciding which side is the Detect and which the Left channel output.

 

4 pin 3.5mm (2.5mm) plug connector layout
4 pin 3.5mm (2.5mm) plug connector
at the female miniplug connector

at the circuit board (5-pin)
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Apple iPod Touch 2G Internal 5-pin circuitboard connection visual pinout:
Apple iPod Touch 2G Internal 5-pin circuitboard connection  diagram
click to enlarge
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