What makes a good leaving group?
Any time a new bond is formed, take a look at the atom that’s accepting the lone pair of
electrons. Does it have a full shell of electrons? Oftentimes it does.
If so, that means you’regoing to have to break a bond that’s attached to that atom. If it’s a single bond you’re
breaking, what you end up creating is called a
Note how the second arrow always shows a pair of electrons going
the leaving group.That means the charge on it is going to become more negative by 1 when it leaves. So if the
leaving group is positively charged, it will become neutral, and if it’s neutral, it will become
negative.The identity of the leaving group is crucial to whether the reaction will happen at all. There
are “good” leaving groups and there are “bad” leaving groups. Reactions are more likely to
take place when you can displace a good leaving group.
What makes a leaving group “good” or “bad”? Thankfully, there’s one simplifying
factor tolook at when deciding this: its
Good leaving groups are weak bases.
How do we know what are weak bases? There’s a useful tool for that –
it’s called a pKa table.
Many pKa tables only specifically give you the identity of the acid, but if you think about it,it also gives you information about the
of each acid. The conjugate base is thepart left over when you lose H+.
The stronger the acid, the weaker the conjugate base.
And the weaker the conjugate base, the better the leaving group. So a pKa table is a greatguide to leaving group ability.