Bromocyclohexane and Catalysts Producing A Compound

[Sportfreunde]

I got the part about this being an Sn1 reaction, but my textbook's solution manual doesn't really say how to get A and B meaning that it's supposed to be an easy problem but I can't get it after googling. The question is to find A and B and the stereochemistry.




Btw, there's also a C and D formed from a third and fourth catalyst in the problem which I didn't include in this picture because I understand that part. But the molecule given as B would be impossible to react with a third catalyst (NaOMe, MeOH) wouldn't it?

[chrisf]

Sorry, replying on my phone... What happens when a bulky base is added to a secondary alkyl halide? I'll go over the rest later and post a little "cheat" sheet for you.

[Sportfreunde]

My guess is that the oxygen will displace the Br. I'm not sure if it would displace the ring or not.

[chrisf]

A bulky base like t-But-Oxide will promote Hoffman Elimination. Your product labeled 'A' should be cyclohexene. This happens because of steric hindrance. t-But-Oxide is too large and bulky to initiate a substitution reaction.