Sound only coming from one speaker

My son had an iPod Touch 4.  One day, one channel stopped working.  I hooked his earbuds up to my iPhone and both speakers worked.  We hooked different earbuds up to his iPod Touch 4 and  only one speaker played so we figured the iPod jack had gone bad. 
Today, he won a brand new iPod Touch 5 from a contest at our church.  He sets everything up, syncs up with iCloud and only one speaker is working.  This is using the brand new earbuds that came with the iPod Touch 5.  I call Target, they say to come in to exchange it.  We return the iTouch 5 and get another brand new one.
On the way home, he begins to setup the iTouch 5 and when he slid the unlock slider, he heard the "click" in both earbuds so we thought everything was great.  We get home, he syncs up with iCloud and low and behold, only one earbud is working.  I plug my Klipsch earbuds into the new iTouch 5 and only one earbud is working.
What in the heck is going on?  Apparently this has nothing to do with his device, but something within iCloud or iTunes?  Even stranger thing is it only plays one speaker even with Youtube, Video Chat and Netflix. 
I can "barely" hear music coming out of the speaker that is not working.  It's almost like the audio is panned or faded to one channel.
Any suggestions?  What would cause one audio channel to stop working when he syncs up to his account?
Thanks in advance for your help.

You are pushing the headphones all the way in, or you have a case that is preventing you from doing so. The plastic on the headset jack should be flush with the body of the Touch.

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