Will we be able to upload our mind on a computer? What problems may we encounter? Lets start with the second question, and try to make a conclusion that may be a possible answer to the first.
Lets imagine a machine that can read your mind, every thought and memory, every brain-cell, synapse, neuron, all the way down to the quantum position of every electron. Downloaded and running, it will be your conscious mind at reading time, and it will keep running like your brain.
First question. Which is you? Will you sense the consciousness of both, will consciousness swap, or will you just make a very identical twin? I think most of us will chose the last answer. Why could the reader take the consciousness out of your mind? And could the consciousness be connected? These questions put some doubt on the possibility. To look at some examples on how sci-fi have solved this, I think the answer to the teleporter conundrum is the most interesting. How do you know that you don't kill the transported person, and make a copy that just believe he is you? He is a copy of you, and got all your thought, but your consciousness is gone, and another is in your place. Star Trek answered this by saying that you can feel yourself on both places, before materializing at the destination. It's easy, when the answer, is what ever you can make up.
Second question, or string of questions. What is consciousness? Will AI become conscious? Can you make a synthetic consciousness? I basically made questions I can't answer. But I will try to draw a picture of what I believe consciousness represent. A common definition of consciousness is the capability to observe your surroundings trough your senses, and refereeing to the opposite as unconscious, like when you are knocked out, asleep or drugged. An even if this fits one definition of consciousness, it ignores the fact that your mind still plays out your dreams, and the YOU inhabiting your mind is there. Isn't the YOU inhabiting your mind, the main part of being conscious? I believe so. And therefore the YOU is mine definition of consciousness. It's at least the part relevant. If its not, you can claim that a powered on camera is conscious, because it observe it's environment. Back to, will AI become conscious? We probably need to know more about what consciousness is, to answer that question. Consciousness in this case being the YOU. Can you make a synthetic consciousness. I will just reply yes. If biology can, we probably will be able with time, maybe even without knowing what consciousness is.
In my conclusion, I will give my solution to some of the issues above, and also give my solution to the problem may see in AI reaching singularity and make human completely obsolete. And that is computer brain implants. We already made life critical cyborg implants like peacemakers, and artificial body-parts. Other machines to mention is dialysis machines and life-support systems. Nano-robots and interactive pills are in the making. Computer brain implants, may sound far-fetched, but in a world where "basic" information take more and more time to accumulate, an easier way on gaining information may be needed. Also with AI coming a better, faster and more precise way of communicating with computers may be needed. Not to forget the need to keep up with computers. A computer brain implant could give us the ability to do faster calculations, and sort facts, myths and feelings. I believe this also is the road to mind upload, where first stop is the mind/machine connection made by the implant, the next step is implants where consciousness can exist, and the last step, like Ship of Theseus switch every part until synthetic brain is the only one left. Making the Start Trek answer the solution in a more doable way.