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Jun 7, 2015 6:32 PM in response to rudyt2039by den.thed,What year model iMac is it...? https://support.apple.com/en-us/HT201634
The newer models have a single headphone jack port and the older models have both input and output jack ports.
If you have an older model with both input and output ports, check to make sure that you are plugging your headphones into the output port.
Likewise on both models if you open the System Preferences for Sound and select the Output tab, you should be able to see it switch from the Internal Speakers to Headphone output.
Additionally if you are seeing the sound output preferences switching, then perhaps your headphones are bad and you need to try another set of headphones.