Lol I was exact same

how did you get on 😂

😂 me

How did your test go??

Same

for point 2, both can happen

A stronger acid is the opposite of more favorable, strong acids have weak conjugate bases (that are stable) and therefore willing to donate their proton more than other acids (to get to that more stable conjugate base). So it will never be favorable to form a strong acid, rather it's favorable for the strong acid to protonate another species and become the weak, stable conjugate base (Cl-)

It is theoretically possible for that chloride ion to bump into that proton and grab it, but that forms HCl, which will be very good at getting rid of that proton as soon as it gets its hand on it. When we do these mechanisms we kind of just have to look at the bigger picture.

Was wondering same

So HCl is a very strong acid, in an aqueous solution it will completely dissociate. It's also not something that will really like to form because nature doesn't like forming strong acids as products. Adding pyridine will give somewhere for that acidic proton to go and also serve as a counter-ion for the chlorine anion. That will make this entire reaction go a lot quicker. However, if you don't do this in pyridine, you may be able to write the products as an equilibrium with carboxylic acid + chlorine atom carboxylate and hydrochloric acid. Personally, I would write this as favoring the reactants. I am also an orgo student so take my advice with a grain of salt.

In a basic solution with pyridine, you'll probably end up with the carboxylate salt and pyridinium chloride. Depending on the pH, you may need to add a dilute acid to get the carboxylic acid.

I feel you man. It feels like an impossible maze

Happy Chemist no