REGIOCHEMISTRY AND STEREOCHEMISTRY OF EACH OF THE FOUR MECHANISMS:

It is OK to have more than one product for a reaction. For example, it is OK to determine that SN2 and E2
are competing and that you get products from both mechanisms at the same time. There is nothing wrong
with that. There does not have to be only one answer. But there are a few extra pieces of information that
will help you determine if there is one or more than one mechanism operating:

1. Some reagents are excellent nucleophiles but are not good bases. Some reagents are excellent bases
but are not good nucleophiles. You should be familiar with certain reagents:
• Nucleophiles (that do not act as bases): F-, Cl-, Br-, I-, CN-, RS, RSH. When you see these reagents,
you do not need to worry about elimination reactions.
• Bases (that do not function as nucleophiles): H -. When you see this reagent, you do not need to
worry about substitution reactions.
• Most other reagents that you will see can function as either a base or a nucleophile.
2. Look at the temperature, if it is given. High temperature (like 100°C or higher) will favor elimination
products. Low temperature (like room temperature) will favor substitution products.
3. Bimolecular reactions are generally faster than unimolecular reactions. So, all things being equal, SN2
will be faster than SN1, and E2 will be faster than E1.

Example: Predict the products of the following reaction:

Answer: We need to ask our three questions:

1. What kind of reaction is taking place?

We see that we have a substrate with a leaving group, so we need to consider substitution and elimination
reactions. The reagent is a good nucleophile, but it is not a good base, so we only need to worry about
substitution reactions. We need to determine whether we have SN1 or SN2. Let’s go through all four
factors:
• The substrate is secondary, so that doesn’t help us much.
• The nucleophile is pretty good (it has negative charge) so that favors SN2.
• The leaving group is good (but not excellent and not bad) so that doesn’t tell us much.
• The solvent is a polar aprotic solvent. This tells us that we have an SN2 reaction.

Now we know what reaction is taking place (SN2), so we ask our last two questions:

2. What is the regiochemistry? Not applicable. The nucleophile attacks at the carbon that bears the leaving
group.

3. What is the stereochemistry? Inversion.

Now we are ready to draw our product. We replace the Br with a CN group and we invert the stereocenter: