I am told that the nucleophilic chloride anion attacks the tri-substituted location because it has the most partial positive character due to its ability to stabilize positive charge.
How does that statement make any sense?
I'm not following his train of "logic," which is as follows:
The nucleophile will want to attack the location with the greatest partial positive charge. Okay, Coulomb's law. I'm good with this statement.
The carbon with the greatest partial positive charge is the one that can best stabilize positive charge. (?)
Alkyl groups are slightly electron-donating; the tertiary carbon will be able to better stabilize partial positive charge.
Thus, the chloride anion attacks the tertiary rather than the secondary carbon. I don't see how this follows from the previous assertions. Doesn't stability correspond negatively with reactivity? If so, what is the real reason the chloride anion attacks the tertiary carbon rather than the secondary carbon?