[henrytudorvii]

So I have this reaction pathway and I am supposed to write down the Mechanism and the conditions/reactants needed.



I'm fairly certain that I am headed in the right direction, but I would like to know whether I am correct.

I know that I have to remove the bromine atom. For this I am going for a SN1 removal to leave the carbocation to let it bond with the negative charge that will be formed on the other end. In order to favour SN1 I would use a polar protic solvent such as water or formic acid. In addition I would use a base like NaOH to remove to remove a proton from the other end of the chain and to leave a negative charge via enolization. The carbocation and the negative charge would hopefully attract forming the final compound.

[anna.kolinski]

Use LDA as a base to form the enolate first. LDA is a bulky base, and so will allow remove the 'kinetic' proton. The kinetic proton is the one which is most sterically accessible i.e. the one on carbon 9.

Now you will have an enolate with a C=C double bond between carbons 8 and 9. You can now reform the C=O bond, and do a curly arrow from the C=C double bond, to the C-Br, and knock off Br.

I think anyway