Hi guys, its 12 hours to my final exam and i really need help with this question. I have posted this in a previous thread but forgot to add the Br!
I need to complete this synthesis using any reagents in 3 steps or less
Thanks very much for your help.
Hmm... that's ever so slightly easier!!
In fact you could probably use the information in the thread here to apply it to the correct question; all you needed to know is how to do the elimination step.
1.) 1-bromo-2-cyclohexyl ethane -----------> 1-cyclohexyl ethene
Dehydrohalogenation using NaOEt and EtOH
2.) 1-cyclohexyl ethene ---------------> 1-cyclohexyl ethane-1,2-diol
Hydroxylation using following reagents
(i) Cold aqueous alkaline KMnO4
(ii) OsO4 followed by hydrolysis
I think that the first step is not so great. Although NaOEt is fine if the primary bromide was more hindered, I just think it isn't hindered enough so you may get a SN
2 reaction instead, or both SN
2 and E2 reactions. Bases like DBN, DBU, KOCEt3
-Bu would be better as they are hindered nucleophiles.
Also I would name the product of the first reaction vinylcyclohexane or at least cyclohexylethene; there is no need for the spaces between the cyclohexyl bit and the ethane/ethene bit.
(the_negro_puppy: please stick to one thread for one 'topic
', and good luck in your exam!