Destroyer #44

[WOAHHI]

Hi all - I was wondering if anyone could tell me why when we are in an acid we attack the most substituted carbon and why in a base we attack the lease substituted carbon. I remember reading the explanation somewhere but I am having a hard time going through all my materials and still can't seem to find it so it's bugging me. Thanks!

---

Members don't see this ad.

 

[AndyK]

Hi all - I was wondering if anyone could tell me why when we are in an acid we attack the most substituted carbon and why in a base we attack the lease substituted carbon. I remember reading the explanation somewhere but I am having a hard time going through all my materials and still can't seem to find it so it's bugging me. Thanks!

The acidic attack is an Sn1 mechanism while the basic attack is an Sn2 mechanism. In Sn1 the most important factor is the stability of a carbocation, while in Sn2, the hinderance of nearby groups comes into play, so the less substituted the carbon, the better.