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Topic: LDA, Enolate, and a More Substituted Carbon  (Read 1430 times)

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Offline Tuck82er

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LDA, Enolate, and a More Substituted Carbon
« on: April 18, 2013, 12:07:49 AM »
So I have 2-methyl-1,3-cyclohexanone and I react it with LDA in THF. When working with LDA typically the trend is that a proton is removed at the less substituted carbon. However one of the answers in the my text says that the proton will be removed at the more substitued 2 carbon of the ring, where the methyl group is also bonded. Does this occur because the protons at that carbon are very acidic? Just wanted some conformation as this goes against my understanding of LDA/THF.

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Offline discodermolide

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Re: LDA, Enolate, and a More Substituted Carbon
« Reply #1 on: April 18, 2013, 02:10:24 AM »
The presence of two carbonyls in the 1,3 arrangement make the CH proton very acidic, compare with ethyl acetoacetate.
Usually sodium hydride is strong enough to deprotonate this proton.

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