Well do you just want the answers or what don't you understand?
Do you know what ozonolysis followed by a reductive work up gives you? Do you know how to make an ester?
Have you heard of the Pinacol-Pinacollone rearrangement? Do you know how to remove carbonyl groups?
Last edited by illusionz; 06-06-2012 at 18:35.
Usually I'd recommend diazomethane for conversion from an acid into a methyl ester, but in this case you also have a ketone so run the risk of CH2 insertion next to it. The safest way would be reaction with methanol and an acid catalyst. Diazomethane would probably be ok as the COOH proton is more reactive than the ketone C=O. Acid/alcohol esterification is an equilibrium so wouldn't give you an amazing yield, and the diazomethane method could have side reactions. I'm not sure which would give the best yield, but if I had to guess I'd reckon the diazomethane one would be better as long as you only use one equivalent.
(Original post by ScaryKid_ScaringKids)
Sorry, I should have been more clear, I'm just clueless about part ii) for both questions and I think I have the mechanism for the first question wrong. I don't know what to do after I get:
Thanks for the help so far, I really appreciate it
As for part b) removal of carbonyl groups can be done by several methods.
The most tolerant for other functional groups is reaction with a di thiol and BF3 to form a thioacetal (the sulphur analogue to an acetal), which is then cleaved with Raney Nickel.
Another is the Wolff Kishner reduction. Reaction with hydrazine and hot conc OH-.
Lastly the clemmensen reduction. Zinc dissolving in conc HCl. But this can only really be used when the C=O is the only functional group present.
In this case any of the three above methods is fine.
(You could also reduce to the alcohol, tosylate then reaction with BH4- [a source of nucleophilic H] but this is more steps)
Last edited by illusionz; 08-06-2012 at 00:24.