What's the reaction of isopropyl chloride with sodium acetate? (The solvent is acetic acid)
Is it SN1 or SN2?
It's not that difficult to approach isopropyl chloride's carbon, for there isn't much steric crowding. It's just a 2 degree alkyl halide with two methyl groups. This favours SN2.
The carbocation formed by the 2 degree alkyl halide, here in this case, is stabilised by the +I effect of two methyl groups and also six hyperconjugative structures. This should favour carbocation formation, hence SN1.
Acetic acid is a polar protic solvent, and can solvate sodium acetate.
Acetate ion isn't a great nucleophile (or is it?). I'm not sure, here. I know that acetic acid is a weak acid, so acetate ion is a strong base but I believe its nucleophilicity is suppressed by solvation.
Chlorine isn't an amazing leaving group.
So, does SN1 take place or SN2? Could someone also give some experimental data to support their reasoning?
Here's something I found, it says that both SN1 and SN2 can occur. Now which one occurs here, is probably decided by the nucleophile? I'm not sure. Anyway, thought I'd put this table up here for reference:
Source: Organic Chemistry - Clayden - Oxford University Press - 1st edition - Page 424
Edit: Someone in the comments section said that you can't predict which mechanism is major, and have to look for experimental facts. So, for the sake of the completeness, where are the facts? Could someone please post the relevant details as an answer?