[a confused chiral girl]

Hi,

I am confused if the diagram that I have drawn below would work. Can someone please tell me if my try at this question makes sense or not? I choose to use H2O, and H+ to perform hydration first, and then add PCC reagent to oxidize it into a ketone so we can add the amine to get the final required product.

thank you!

[Custos]

That looks okay to me.

[AWK]

This is multi.bmp

[movies]

You could get mixtures of alcohols from your first step by hydride shifts from the carbocation.

Do you know another way to turn an alkene into an alcohol?

There are two major methods which give one of the two alcohols selectively without giving the rearranged products you get with acid and water.

[a confused chiral girl]

You could get mixtures of alcohols from your first step by hydride shifts from the carbocation.

Do you know another way to turn an alkene into an alcohol?

There are two major methods which give one of the two alcohols selectively without giving the rearranged products you get with acid and water.

Another way to turn an alkene..would be using Jones Reageant to turn aldehyde into an alcohol? so you mean, the first step would be better to use Jones Reagent rather than H20 and H+?

[kiwi]

no thats not quite it, think about what type of alcohol you want to get out. one way involves an atom you don't generally think about using much.

[Dolphinsiu]

http://en.wikipedia.org/wiki/Oxymercuration_reaction

First step: 1. Hg(OAc)2
               2. NaBH4

Do you still remember what is the purpose of oxymercuration + demecuration ?

[a confused chiral girl]

just want to let others who may still be interested in this question know, the last step is actually not correct. H+ has to be added with CH3OH in the last step to get the product.