Probably not, but if you used an HDMI audio extractor you could get a Optical output.

https://www.amazon.com/Optical-Toslink-Bi-Directional-Converter-Splitter/dp/B084T4QDFP/

Nope.

you would need something like an HDMI extractor. That would give you a 3.5mm output port without using the system headphone jack.

https://www.amazon.com/Optical-Toslink-Bi-Directional-Converter-Splitter/dp/B084T4QDFP/

This HDMI adapter should work, or this analog converter. The latter is more future-proof if you ever upgrade your monitor (as long as the new one also has analog audio out).