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17.9: Alkylating the B-carbon
Terms in this set (13)
Nucleophiles react with alpha, beta unsaturated aldehydes and ketones, forming either __________ or __________?
direct addition products and/or conjugate addition products
Nucleophiles react with alpha,Beta-unsaturated aldehdyes and ketones forming either direct addition products and or conjugate addition products. When does conjugate addition predominate?
When the nucleophile is a weak base
Are enamines strong or weak bases?
What do enamines attach the alpha carbon of an aldehyde or ketone to in regards to alpha, beta unsaturated carbonyl compounds?
Enamines, which are weak bases, attach the alpha carbon of an aldehyde or ketone to the B-carbon of an alpha,Beta-unsaturated carbonyl compound via conjugate addition
When you alkylate the B-carbon via an enamine, what is the product?
What are the two ways to alkylate the B-carbon?
You can alkylate the B-carbon via an enamine or a Michael Reaction
When the nucleophile in a conjugate addition reaction is an enolate ion, what is the reaction called?
a Michael reaction
What are enolate ions that work best in Michael reactions formed from?
carbon acids that are flanked by two electron-withdrawing groups. That is, enolate ions of B-diketones, B-diesters, B-keto esters, and B-keto nitriles!
In the michael reaction, why does conjugate addition occur?
Because the enolate ions of B-diketones, B-diesters, B-keto esters, and B-keto nitriles are weak bases!
What kind of compounds does the Michael reaction work for?
a,B-unsaturated aldehydes, ketones, esters, and amides!
What is the product of the Michael reaction?
Why does the michael reaction work with the a,B-unsaturated esters and amides?
Because of the low reactivity of their carbonyl groups
If either of he reactants in a Michael reaction has an ester group, what must be true about the base?
the base used to remove the alpha-proton must be the same as the leaving group of the ester
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