I told you that Ozone is the only electrophile in this series that will stand up to the big
bully, the nucleophile, or in this case the alkene.
I have a question here, what does Ozone tell an alkene before an Ozonolysis?
Just to give you an idea, Ozone knows that the nucleophile is going to attack him.
He knows he’s going to be destroyed, but he tells him this, here’s the answer.
Ozone tells the alkene, you break my record.
Now I break you like I break your friend.
This is from the Motion Picture Bloodsport, 1988, if you haven’t seen this movie, I recommend
it.
Basically, Ozone is telling the alkene, yeah, I know you’re going to destroy me by
before you, you destroy me, I’m also going to do something, I’m going to break you.
So it’s the only electrophile that stands up to the bully.
This slide shows you a simplified methodology, how I want you to remember Ozonolysis.
Imagine that you’re going to fix your hands this way, where you have two fingers, and
then both of them point at each other.
So each fist represents a carbon, and each set of fingers represents one bond.
So you have a sigma and a pi bond right there, that is your alkene, or double bond.
Here’s your carbon, here’s your carbon, and here are your two fingers, right?
So we’re going to break each alkene in half, and we’re going to do Ozonolysis on
each of these two reactions, but then in one, we’re going to do a reductive workup with
dimethyl sulfide, and on the other one, we’re going to do an oxidative workup with hydrogen peroxide.
Let’s go to the top one.
Step one, you’re going to break the double bonds.
I want you to visualize this, you’re going to break the double bond, and on each tip
of your finger, you’re going to add an oxygen on each side.
So then, basically what you have accomplished here is making two carbonyl groups on each
hand.
That’s what we’re doing here, we’re going to break the alkene in half, and we’re going
to add oxygens to each tip of the breakage.
Then, step two, since it’s a reductive workup, an aldehyde here was formed on the right side,
so this is an aldehyde, it stays as the aldehyde, and on the left side, you made a ketone.
Both of these compounds stay.
Now, if we do the second reaction, the first step is to break off the alkene and put oxygen
on each end of the breakage, meaning put it on your fingertips.
Then at this point, you have made a ketone and an aldehyde, but because this carbon-hydrogen
bond is easy to break, the moment that you use hydrogen peroxide, you can do what is called
an oxygen insertion, which is a further oxidation stage, and this oxygen is going to add in between
that carbon and the hydrogen.
So now, you end up with a ketone on the left side and a carboxylic acid on the right side.
