Leaving Groups

A leaving group , LG, is an atom (or a group of atoms) that is displaced as stable species
taking with it the bonding electrons. Typically the leaving group is an anion (e.g. Cl-) or a
neutral molecule (e.g. H2O). The better the leaving group, the more likely it is to depart.
A "good" leaving group can be recognised as being the conjugate base of a strong
acid.
What do we mean by this ? First we should write the chemical equations for the two
processes:

These two equations represent Bronsted acid dissociation and loss of a leaving group in a
SN1 type reaction.
Note the similarity of the two equations: both show heterolytic cleavage of a s bond to create
an anion and a cation.
For acidity, the more stable A- is, then the more the equilibrium will favour dissociation, and
release of protons meaning that HA is more acidic.
For the leaving group, the more stable LG- is, the more it favours "leaving".
Hence factors that stabilize A- also apply to the stablisation of a LG-.
Here is a table classifying some common leaving groups that we will eventually meet......

Note, once again, that HO- is a poor leaving group (remember from the reactions of
alcohols ?).... after all its the conjugate base of water.... and when we turn on a tap in the
kitchen, we aren't usually trying to get a strong acid to drink !
But water itself, H2O, is a good leaving group, since it is the conjugate base of H3O+, which is
a strong acid.

Nucleophile: A molecule that has a negative charge or at least a lone pair of electrons. Here
are two examples of a nucleophile:

*You should notice that compound (A) not only has three lone pairs of electrons but also has
a negative charge. It is this negative charge that helps to make -SH an excellent nucleophile.
You should also notice that molecule (B) has two lone pairs of electrons but no negative
charge. SInce (B) does not have a negative charge it is an "okay" nucleophile, but not so
great.
There are many nucleophiles, however here is a list of the ones that you should memorize. I
have written them down in descending order. The top of the list shows the best nucleophiles
and the bottom shows the nucleophiles that are not "so great". You are also responsible for
memorizing them in this order. Here is the list:

Leaving Group: A atom or group of atoms that gets kicked out

of a molecule. This
leaving group is usually replaced by a nucleophile. Here is a list of good leaving groups that
you must memorize. The best leaving groups are at the top of the list and the ones that
are"okay" are at the bottom of the list. However, please note that all of the leaving groups on
the list are relatively good leaving groups.

* Also note that OTs is the

best(ultimate) leaving group

Nucleophilic Substitution Reactions

Substitution reactions are reactions that
occur when a nucleohile replaces a leaving
group within a molecule. When substitution
occurs, it almost looks like the leaving group
is being kicked out by the nucleophile. Let's
look at the example below:

First, you should recognize the nucleophile (-SH),because it is the one with the negative
charge on it. Notice how the nucleophile attacks the carbon with the good leaving group (Br)
directly attached to it (see the carbon with the star attached to it). Finally, the leaving group
leaves and the nucleophile attaches to the carbon where the Bromine once was.
*When I use the word attacks it means that the nucleophile is using two of its' lone pair of
electrons to form a bond between the nucleophile and the carbon where the leaving group is
attached.
There are two types of nucleophilic substitution reactions.The first type of reaction is called
the Nucleophilic Substitution Bimolecular Reaction also known as SN2. The second type of
reaction is called the Nucleophilic Substitution Unimolecular Reaction also known as SN1.
Even though both of these substitution reactions are similar they each possess different
properties which make them unique. Therefore, we will go through each reaction separately.