OCHEM SN1 and SN2 Major Products

[cathy]

Homework Statement

Determination of Major Products in SN2 reactions?
What would be the major product of 2,3-dichloro-3ethyhexane reacted with:
1. one equvalent of NaI in acetone?
2. one equavelent of AgNO3 in methanol
and explain your reasoning.

Homework Equations

N/A

The Attempt at a Solution

I understand the first one. Iodide would be your nucleophile (Nu) here. The Cl on the C3 will not undergo Sn2 b/c the C3 is tertiary. But the Cl on C2 will in fact work for Sn2 b/c it is secondary. So the product would be 3-chloro-3-ethyl-2-iodohexane.
For the second once, with the AgNO3 in methanol, I am confused.
Would this reaction even occur? If so, could someone explain to me why?

 

[Saitama]

Homework Statement

Determination of Major Products in SN2 reactions?
What would be the major product of 2,3-dichloro-3ethyhexane reacted with:
1. one equvalent of NaI in acetone?
2. one equavelent of AgNO3 in methanol
and explain your reasoning.

Homework Equations

N/A

The Attempt at a Solution

I understand the first one. Iodide would be your nucleophile (Nu) here. The Cl on the C3 will not undergo Sn2 b/c the C3 is tertiary. But the Cl on C2 will in fact work for Sn2 b/c it is secondary. So the product would be 3-chloro-3-ethyl-2-iodohexane.
For the second once, with the AgNO3 in methanol, I am confused.
Would this reaction even occur? If so, could someone explain to me why?

The second one proceeds by SN₁ mechanism with Ag⁺ snatching out a Cl^- from the tertiary carbon. Do you see why the Cl^- from tertiary carbon is removed?