Nucleophilic Chemistry part 2

Elimination Reaction
As mentioned in part 1, not every single halogenoalkane reaction is a substitution reaction.

The exception is an elimination reaction, which is very specific, so you should be able to recognise when it
occurs.

What to look for?

The big clue is when they use ethanol as the solvent and OH- ions from something like KOH. And an
alkene is the product.

It must be these conditions: OH- dissolved in ethanol. Anything else gives the normal substitution

So anytime you see a halogenoalkane you can assume it's substitution unless you see these very
specific conditions.

For example, if you see ammonia in ethanol, it is still nucleophilic substitution. You need the OH -
/ethanol combination.

So whats going on here?

You must know the OH- ions are acting as a base and not a nucleophile.

You do not need to know the mechanism but it is actually much easier to see what is going on if you
at least look at it below.

In a nucleophilic reaction the OH- would attack the positive charge on the carbon atom but as we can see
below, this doesnt happen:

As the OH- ion is acting as a base it accepts a proton (a hydrogen). The definition of a base is a proton
(hydrogen) acceptor. The OH- "removes" a hydrogen atom from the haloalkane, which is simply down to
these specific conditions.

remember 99% of the time when you see a haloalkane you will be doing nucleophilic substitution.
Secondary haloalkanes
Another exam favourite is to mention that there are three products from an elimination reaction. This
usually is the case for an unsymmetrical secondary halogeonalkane.

The reason for this is that different hydrogens can be removed in the first step of the mechanism. Below
is just the same as we did above:

But here we have removed a H atom from the other side of the C-Br bond, which gives an alkene that can
do geometric isomerism giving two further products:

As I said above the mechanism is unnecessary but it can aid you greatly as you can work out the
products and know why they are formed. It is actually much easier to understand what is going on
having seen the mechanism then remember the relevant parts:

Very specific conditions: OH- in ethanol

OH- is acting as a base (hydrogen acceptor)

Three products possible for an unsymmetrical

secondary halogenoalkane due to E/Z
isomers