Can you plug in headphones to the 3.5mm headphone jack to USB C adapter, and then plug this USB adapter with headphones plugged in, to, the USB C multi adapter(hdmi, usb c, usb a) through USB C female socket, and this multi adapter to iPad?

Both the multi adapter, and the 3.5mm adapter are original apple products, and, yes it does work without the multi adapter, but I want to be able to use it this way, since I want to use the usb-a port to connect my guitar to ipad and hear the sound coming from garageband through the headphones via the usb c port at the same time. If you have any other solutions for this, it would fit me as well

There is iRig for this purpose I know, but dont want to pay for it.

I mean like that: