So, the very first thing that leaps out to me is that - despite your framing - I'm not entirely convinced anything egregious has occurred. This may very well be due to you wanting to be circumspect, but let me explain what I see.

What you've pointed out are typos in handouts (who the fuck cares?) and that you don't feel the survey of the field for undergrads was in-depth enough (ok?). You mention factual errors, but don't provide specifics.

Even if I take you at your word, the correct approach is not to go to the department chair as a PhD student. That is often a recipe for disaster.

Go to your advisor (or another faculty member whom you trust) with these concerns. Bring them concrete examples and ask them if they believe it is serious and, if so, what you should do. Follow their advice.

They might tell you that you're absolutely correct and this needs to be addressed and they might tell you you've made a mountain out of a molehill. As a general word of advice, as a PhD candidate calling tenured professors 'failure[s]' isn't the best way to go about things.