Q. 17
Isopropyl chloride undergo substitution by
Answers
My thoughts:
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?
Answer:
SN1
Explanation:
Due to steric factor , isopropyl chloride can not undergo SN2 reaction but since the carbon in C-Cl is 2° ,it forms a stable carbocation due to six hyperconjugable hydrogen and the inductive effect of CH3.Hence, it undergoes substitution by SN1 mechanism.
ISOPROPILE CHLORIDE :- (CH3)2C-Cl