WOAHHI

10+ Year Member
Dec 28, 2008
78
0
Status
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!
 

AndyK

10+ Year Member
7+ Year Member
Sep 24, 2007
530
4
Houston, TX
Status
Pre-Medical
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.