I don't see why it's not possible.
In your example scenario, it sounds like Bob is vibe-coding a project in assembly language, and then using an existing assembler to create the final binary?
I have not tried it, but I would imagine that current LLMs are relatively weak on generating assembly language, just due to less thorough training compared to higher-level languages, but even if so, that's surmountable.
As for, what I think you are suggesting, having the LLM also do the assembly step? Again, in theory, sure, but I would think just using the existing known-good assembler would be preferable to training an LLM to convert assembly language to binary. I'm not sure what you would gain in terms of either speed or overall productivity to have the LLM itself do the assembler step?
