00:01
So we have the following bridge bicyclic compound, and we want to try to understand why the tertiary alkyl bromide does not undergo either e1 or e2 elimination reactions.
00:13
So recall for e1 elimination reactions, this requires a carbocadine intermediate, which is planar.
00:21
This would cause too much ring strain and angle strain on our bridgehead carbon.
00:25
And i'll go ahead and circle – i know there's two bridgehead carbons, but i'll circle the one that i'll be talking about, which is a lot.
00:30
This one in red.
00:32
And so this is kind of a violation of brett's rule, if you recall, or if you learned before.
00:38
So i'm going to go ahead and write that down real quick.
00:42
So i would say that our e1 requires planar sp2, hybridized carbocation intermediate.
01:15
And as a result, this would cause, so which would cause too much ring strain and angle strain on our bridgehead carbon...