[cofi]

I did the following experiment:
2mL of 2% AgNO₃ ethanolic solution was added to three test tubes
then, in each test tube, I added 2 drops of:
1. ethyl-bromide -> no reaction
2. isopropyl-bromide -> slow reaction
3. tert-butyl-bromide -> immediate reaction

but I'm not really sure what happens?
here is what I think:
R-Br -> R⁺ + Br^- (1)
Ag⁺ + Br^- -> AgBr (2)
R⁺ + H₂O -> ROH₂⁺ (3)
ROH₂⁺ + NO₃^- -> ROH + HNO₃ (4)
(I mean, ROH₂⁺ + H₂O -> ROH + H₃O⁺ (5), and with NO₃^- present there, it's effectively HNO₃)

if it's AgNO₃ in >=96% EtOH then the EtOH is likely to do the water's dirty job: solvolysis (3) and collecting protons (5)

[fishyuyue]

I did the following experiment:
2mL of 2% AgNO3 ethanolic solution was added to three test tubes
then, in each test tube, I added 2 drops of:
1. ethyl-bromide -> no reaction
2. isopropyl-bromide -> slow reaction
3. tert-butyl-bromide -> immediate reaction

but I'm not really sure what happens?
here is what I think:
R-Br -> R+ + Br- (1)
Ag+ + Br- -> AgBr (2)
R+ + H2O -> ROH2+ (3)   (No water in AgNO3 ehanolic solution)
ROH2+ + NO3- -> ROH + HNO3 (4)
(I mean, ROH2+ + H2O -> ROH + H3O+ (5), and with NO3- present there, it's effectively HNO3)

if it's AgNO3 in >=96% EtOH then the EtOH is likely to do the water's dirty job: solvolysis (3) and collecting protons (5)

[cofi]

perhaps you didn't see:

if it's AgNO3 in >=96% EtOH then the EtOH is likely to do the water's dirty job: solvolysis (3) and collecting protons (5)

[fishyuyue]

ROH2+ + NO3- -> ROH + HNO3 (4)( nitric acid is a stronge acid and it can ionizes into H cation and nitrate anions totally

[mir]

This is a classical experiment into studying carbocations.
And it is probably a SN1 reaction happening with an ionic intermdiate that is stabilized in the protic ethanol solvent.

You have figured out much. The nitric acid however is dissociated in the solution. But the solvation shells is associated with eachother.

[SoFTiCE]

Yes!
This Sn1 reaction and r3>r2>r1
you shoul read Murch, reactions in organic chemistry, T1