00:01
So in this problem, we're asked to find the step -by -step reaction that can form cyclohexenol from cyclohexane and cyclohexene from cyclohexenol.
00:12
So what i like to do first whenever we're working with organic synthesis problems is to see which of the functional groups change.
00:22
Because most reactions will change only one functional group and everything else will be untouched.
00:29
So in the first reaction we can see here that we're making an alcohol from an alkan because what's attached to this previous carbon here is only an h.
00:45
So we're making an alkan, turn into an alcohol.
00:49
Now this would be usually really difficult with most reactions that we learned in organic one because h or the alkan group is not reactive at all.
01:00
And the only reaction that we learn that makes a more reactive group from an alkan is called radical bromination or radical chlorination or whatever.
01:16
It's whenever we turn this h into a halogen group.
01:21
And that we get by adding dibromine or dichlorine in the presence of light.
01:29
This works because whenever we have bromine, whenever we have a bromine molecule, this light splits up the electrons so that it forms bromine radicals.
01:45
And this bromine radical will go on to react with this bond here and replace or displace this h and substitute itself into the alkan.
02:00
So that way we get br, so a brominated cyclohexane.
02:08
From here, all we have to do is turn this br into an oh, which is actually not as easy as it looks because, let's say, if we try to just substitute this in with an s &2 reaction, with, let's say, well, our nucleophile needs an oh, so the easiest one would be in a .o .h, right? but naoh is a strong nucleophileisher, but it's also a strong face.
02:38
Okay, this can go either s &2 or e2 reaction.
02:44
And if we use naoh, then we're not going to only get cyclohexenol.
02:49
We're also going to get the eliminated product, which is something that we could utilize since that is our product.
03:05
But for now, let's keep things as pure as possible whenever we're working with reactions here.
03:11
So we're not going to do this.
03:14
We have to take things in two steps.
03:17
The easiest way to do things is to first make the alkyne because we can control that everything undergoes an e2 reaction, but we can't control if everything's going to be substitution.
03:32
And that we do by using a bulky base, such as potassium turketoxide, that will make our cyclohexene.
03:47
And from this cyclohexene, we can turn this back into the cyclohexanol that we want.
03:55
We can use any kind of hydrolysis method, whether it's oxymoceration, demercuration, we can use hydroporation, and it doesn't matter because this alkyne is symmetric.
04:09
But for now, we can be simple and just use h3o plus...