Quick question on Ochem

[Jackthesparrow]

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(d) according to the solution, it is 1) conc. H2SO4 2)BH3*THF 3) H2O2, NaOH

Can you also use t-BuOK, instead of conc. H2SO4?

Thank you!!!

 

[tooth_hurty]

Why would use suggest using a strong bulky base instead of a strong concentrated acid?

 

[Jackthesparrow]

I would of course use strong conc. acid, but what if DAT has t-BuOK and no strong conc. acid as one of their options. Then can we still use t-BuOK to get the same product?

 

[FeralisExtremum]

I don't think you could. Even if you did successfully cause elimination with the bulky base, you'd create this:

Then steps 2 and 3 would create:

Regardless, I think in general we prefer acids for dehydration of alcohols, not bases. I don't think the first elimination step would even happen.

 

[tooth_hurty]

If you wanted to use t-buOK, you would have to use acid first to protonate the OH and make it a good leaving group (as water). Using t-buOK next wouldn't give you the desired product though because t-buOK is a strong bulky base and would form the Hoffman product (in this case the methyl would become an alkene). Hydroboration of the alkene would then give you an alcohol on the less substituted carbon since hydroboration is anti-markovnikov

 

[Jackthesparrow]

Ah. I got it.

Thanks guys!