00:01
All right, so let's look at this substrate, and we're reacting with hbr.
00:17
And we need to find the major product, potentially more than one, of this reaction.
00:24
So i think it's useful here to just go ahead and do the mechanism, because that explains why we get the product that we do.
00:31
So this is addition of hbr across the double bond.
00:35
The first thing that happens is this double bond will swing open and attack the hydrogen.
00:41
And the electrons that were between the bromine and the hydrogen will remain on bromine.
00:45
So the first step of this mechanism is that the double bond swings open.
00:50
And we're going to get hydrogen added to one side of this double bond.
00:55
But the other side of the double bond is going to get a carbocation, which means one of these carbons gets a bond to hydrogen and the other carbon gets a carbokadion.
01:06
And so there's two possible ways this can go.
01:09
I'll sketch them both out below.
01:18
We can get hydrogen added to this side and a carbocation here.
01:30
Or we can get hydrogen added to this side and a carbocation here.
01:36
Which of these is more likely? which of these is more stable? this carbocation is secondary and this carbototene is tertiary.
01:45
And we know that carbocadines that are tertiary or more stable.
01:48
So we should expect that this will be the dominant product, right? this is not a stable and we won't form this...