The art of free radical substitution
There's this thing they do to make haloalkanes and it's pretty magical if you think about in a magical imaginative way, because you're bored of staring at a textbook full of numbers and equations.
Making a haloalkane takes place in a few stages and it goes by the name FREE RADICAL SUBSTITUTION.
And of course with any process there is a MECHANISM. That's what they call it in the exam "draw the mechanism for this reaction" "outline the mechanism for this reaction" "state the mechanism for this reaction"
MECHANISM. I mean it's not really a mechanism, is it? They could have come up with a better name to be fair. Something more creative. But anyway MECHANISM is the word they decide to use.
Here's an example of the chain reactions for the free radical substitution reaction:
methane + chlorine ---> chloromethane + hydrochloric acid
The haloalkane is chloromethane.
So how do we make it? You need to be familiar with all the stages:
The first stage is called INITIATION, which I find quite scary when you read it in a deep robotic voice. :o
But it's not really a very scary stage.
Basically UV light is shone on the chlorine, and the chlorine absorbs it and it breaks the bond between the Cl-Cl chlorine molecule to form FREE RADICALS.
A FREE RADICAL is a complicated way of saying an atom with an unpaired electron (highly reactive) They are radical :o because they've lost one of their electrons and they are free because they can go out and REACT with anyone they choose to. Now that is a name in chemistry which I do appreciate.You represent a FREE RADICAL in an equation by drawing a little dot next to show the unpaired electron. There are lots of dots coming up!
If you illustrate that stage as in your "MECHANISM" it looks like this:
(Yes we are going up a notch with the whole black yellow and purple thing ;D I thought I'd try it out)
The next stage happens in two parts, and it's called
The first bit is where the free radical steals a hydrogen atom from methane to form hydrogen chloride, and oh look a GREEN METHYL FREE RADICAL
In the next stage this green methyl free radical is reacted with chlorine:
And this produces your lovely desired haloalkane your chloromethane! (It's desirable so it has flashy sun ray things coming out of it, but please don't draw or write that in your exam, the examiner will think you're crazy)
The last stage is TERMINATION :o
which in my opinion is probably the scariest stage. I mean say that in a scary voice. And the nature of this stage is to get rid of all the free radicals, and I like them so it's kinda sad. But they are very reactive, and they need to be calmed down to stable compounds, so I guess it's necessary.
The termination step looks like this: (fr stands for free radical)
I remember this stage as lumping all the leftover free radicals together and making them react, either with one of themselves or one of each other.
And there you have your mechanism of FREE RADICAL SUBSTITUTION. There's not much point revising these stages off by heart with the equations and everything because in the exam they're likely to give you another free radical substitution with say fluorine, and other new compounds. What is more important is knowing the nature of what goes on in each stage and being able to construct the equations for yourself. So it's best to practice writing out the whole free radical mechanism with the step by step stages initiation, propagation x2 and termination for making haloalkanes you haven't met before. "I just haven't met you yet" ;)
A helpful mneumonic if you're not very good at remembering the order of the stages is
Initiation, propagation, termination.
It's kind of crap, but until I think of something more funny or better, I have to resort to I play tennis.
If anyone read or got to the end of this post is good at making mnemonics, and one just appears for IPT in your head however rude, please please message me.