It would appear that your lad is trying to communicate his experience and not succeeding -- just as you are clearly trying to connect with him and not spanning the gap.
Overall, my advice is to listen at least twice as much as you talk, and when you talk don't give information or instructions but ask questions that help you clarify what he's trying to tell you. Try hard to ignore the snotty tone of voice and harsh words, just as you would ignore a whiney 2yo's voice when they're frustrated in trying to tell you something they lack the words for. The frustration is supplying the tone, your task is to listen for the message beyond the frustration.
Most kids have trouble at school around the time their brains are re-organizing themselves in preparation for the major brain development that makes it possible to do abstract operations (when they can see themselves and their lives from the outside for the first time ever). There is some considerable brain damage done, and the children end up with a limited capacity to access short-term memory, they are in the process of losing a lot of their childhood memories, and they lose impulse control and the ability to understand cause and effect -- for a while. The whole period lasts about 14 months, with the worst of it happening through about 6 months.
Frankly, there is a lot about school to dislike: bullying (either as a victim or as a powerless witness), expectations, social pressure to conform and to stand out, irrelevant and outdated material, dictatorial teachers, tyrannical administrators, stupid rules, a massive lack of respect for students as individual human beings... None of it is necessarily a valid reason to quit or rebel, but only the people who are empowered to respond accurately to their environments will be able to master them. I mean: if you can hear and respect his dislike as valid, perhaps he (with or without your aid) can learn to deal with it instead of complaining about it or hoping it will go away.