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17 Cards in this Set
- Front
- Back
The conjugate addition is closely related to
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1,2-addition
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What is a conjugate addition is?
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1,4-addition of a nucleophile to the C=C double bond of an Alpha-Beta-unsaturated aldehyde or Ketone
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The initial product of conjugate addition is a resonance-stabilized enolate ion, which typically undergoes ...
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protonation on the Alpha carbon to give a saturated aldehyde or ketone product
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The conjugate addition of a nucleophile to an alpha-beta-unsaturated aldehyde or ketone is caused by ?
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the same electronic factors that are responsible for the direct addition to a saturated compound
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The electronegative oxygen atom of the alpha-beta-unsaturated carbonyl compound of a conjugate addition withdrawls electrons from the _____ _______, thereby making it ....
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- beta carbon
- somewhat electron-poor and considerably more electrophilic than a typical alkene carbon |
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Conjugate addition of a nucleophile to the Beta carbon of an alpha-beta unsaturated aldehyde or ketone leads to ?
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an enolate ion intermediate, which is protonated on the alpha carbon to give the saturated product
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The net effect of the Conjugate addition is. .
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addition of the nucleophile to the C=C double bond, with the carbonyl group itself unchanged
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The _____ ______ is crucial to the success of the Conjugate addition rxn
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- carbonyl group
- The C=C would not be activated for addition and no rxn would occur, without the carbonyl group |
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Primary and secondary amines add to alpha-beta-unsaturated aldehydes and ketones to yield and ketones ...
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beta-amino aldehydes
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Primary and secondary amines add to alpha-beta-unsaturated aldehydes and ketones rxns occur
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rapidly and yields are good
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Primary and secondary amines add to alpha-beta-unsaturated aldehydes and ketones rxns generally proceeds ....
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with thermodynamic control rather than kinetic control
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Conjugate addition of an alkyl group to an alpha-beta-unsaturated ketone (but not aldehyde) is one of the useful ...
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1,4-addition rxns, just as direct addition of a Grignard reagent is one of the most useful 1,2-additions
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Conjugate addition of an alkyl group is carried out by ...
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treating the alpha-beta-nsaturated ketone with a lithium diorganocopper reagent
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Primary, secondary, and even tertiary alkyl groups undergo the addition rxn with ...
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organocopper, as do aryl and alkenyl groups
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Alkynyl groups react ____ in the conjugate addition process
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poorly
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Diorganocopper reagents are unique in their ability to ?
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give conjugate addition products
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Other organometallic reagents, such as Grignard reagents and organolithiums, normally give ...
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direct carbonyl addition on rxn with alpha-beta-unsaturated ketones
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