[Nightheron]

Hey guys, first time here. Glad to be a part of this forum.

My first language is Portuguese.

I have two solvents, Agno3 and NaI. (Silver nitrate in ethanol and sodium iodide in acetone).

I have these compounds:
1-chlorobutane 1-bromobutane 2-chlorobutane 2-bromobutane Bromociclohexane 2-chloro2-methylpropane and 2-bromo2-methylpropane.

Which ones will react first in Agno3 and NaI?

In NaI what matters is the steric hindrance, because it favors sn1 reactions.
So I guess 1-chlorobutane and 2-bromobutane will react fast, the bromine is a weaker base tho, so it reacts fastest. The bromociclohexane is in a ring, so I think it is harder to break. (Little confused here). What about the 2-cholrobutane and 2-bromobutane? What will be the difference? I think it is more hindered, am I right? The bromine and chloro are bounded to two carbons... And in the case of the 2-cloro(or bromo)2-metilpropane, they are bounded to three carbons.

So my guess it that the reactions will be like this, from fastest to slowest. (SN1 with NaI)
1-bromobutane ; 1-chlorobutane ; bromociclohexane (maybe this one is fastest then the 1-chlorobutane?) ; 2-bromobutane ; 2-cholrobutane ; 2-bromo2-methylpropane ; 2-chloro2-methylpropane.

And in Agno3, since is favors sn2 reactions, what matters is the stability of the carbocation. So the terciary ones will react fastest, then the secondary ones, etc.
So between the bromo and chloro, which is the fastest? I think it's the same: The leaving group is better the weaker the base is. So the fastest will still be the compound that has the bromo.
Order, from fastest to slowest.
2-bromo2-methylpropane ; 2-chloro2-methylpropane ;  2-bromobutane ; 2-cholrobutane ; bromociclohexane (I am not sure so help pls) ; 1-bromobutane ;
1-chlorobutane.

Can someone see what did I do wrong and help me explain it a little better pls? TY for reading and in advance for responding! MUCH appreciated.