Organic Chemistry / Carbocation Intermediate Rearrangements
Sign up for free to keep watching this solution

Video Solution: Two stereoisomers of 1-bromo-4-methylcyclohexane are formed ...

Problem

Two stereoisomers of 1-bromo-4-methylcyclohexane are formed when trans-4-methylcyclohexanol reacts with hydrogen bromide. Write structural formulas of: 

(b) The carbocation intermediate in this reaction

Video Transcript

Hey everyone. So, in Part A we showed that we had our alcohol and our methyl group 1, 4 to each other and we showed it not only in the planar structure but in the chair position, so what we need to show now is simply the carbocation intermediate of it. Now, what that's going to look like is we're going to have a positive charge, the only way to generate that however is this alcohol is actually going to be a water in both cases and you only want to get a carbocation doing an SN1 mechanism, where this is going to leave on its own, so we can show them both if we want, what we're going to get from that is we can show our six membered ring, that was horrible, let's try that again, there we go, a little bit better, we can show that we have now a positive charge there, we're still going to have this methyl group, and that positive charge is also going to have a hydrogen coming off, so this would be the carbocation intermediate and the structure and the other one what it would look like is again we have a chair conformation that looks like this, we still have our CH3 but now what we would have is we have just a hydrogen here, after this leaves, and positive charge, okay? So this would be our carbocation intermediate for this reaction. Alright, so I hope this made sense an now let's take a look at part C.

Related Practice Problems

When compound shown below is exposed to an acid, a molecule of water is elimin...

When compound shown below is exposed to an acid, a molecule of water is elimin...

Provide a detailed mechanism for the following transformation. Show all charge...

Provide a detailed mechanism for the following transformation. Show all charge...

Draw the full mechanism for this reaction including rearrangements if pos...

Draw the full mechanism for this reaction including rearrangements if pos...

There is no carbocation rearrangement in reactions where a bridged intermediat...

There is no carbocation rearrangement in reactions where a bridged intermediat...

Which carbocation would not be likely to undergo rearrangement?
...

Which carbocation would not be likely to undergo rearrangement? ...