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17 Cards in this Set

  • Front
  • Back
The conjugate addition is closely related to
1,2-addition
What is a conjugate addition is?
1,4-addition of a nucleophile to the C=C double bond of an Alpha-Beta-unsaturated aldehyde or Ketone
The initial product of conjugate addition is a resonance-stabilized enolate ion, which typically undergoes ...
protonation on the Alpha carbon to give a saturated aldehyde or ketone product
The conjugate addition of a nucleophile to an alpha-beta-unsaturated aldehyde or ketone is caused by ?
the same electronic factors that are responsible for the direct addition to a saturated compound
The electronegative oxygen atom of the alpha-beta-unsaturated carbonyl compound of a conjugate addition withdrawls electrons from the _____ _______, thereby making it ....
- beta carbon

- somewhat electron-poor and considerably more electrophilic than a typical alkene carbon
Conjugate addition of a nucleophile to the Beta carbon of an alpha-beta unsaturated aldehyde or ketone leads to ?
an enolate ion intermediate, which is protonated on the alpha carbon to give the saturated product
The net effect of the Conjugate addition is. .
addition of the nucleophile to the C=C double bond, with the carbonyl group itself unchanged
The _____ ______ is crucial to the success of the Conjugate addition rxn
- carbonyl group

- The C=C would not be activated for addition and no rxn would occur, without the carbonyl group
Primary and secondary amines add to alpha-beta-unsaturated aldehydes and ketones to yield and ketones ...
beta-amino aldehydes
Primary and secondary amines add to alpha-beta-unsaturated aldehydes and ketones rxns occur
rapidly and yields are good
Primary and secondary amines add to alpha-beta-unsaturated aldehydes and ketones rxns generally proceeds ....
with thermodynamic control rather than kinetic control
Conjugate addition of an alkyl group to an alpha-beta-unsaturated ketone (but not aldehyde) is one of the useful ...
1,4-addition rxns, just as direct addition of a Grignard reagent is one of the most useful 1,2-additions
Conjugate addition of an alkyl group is carried out by ...
treating the alpha-beta-nsaturated ketone with a lithium diorganocopper reagent
Primary, secondary, and even tertiary alkyl groups undergo the addition rxn with ...
organocopper, as do aryl and alkenyl groups
Alkynyl groups react ____ in the conjugate addition process
poorly
Diorganocopper reagents are unique in their ability to ?
give conjugate addition products
Other organometallic reagents, such as Grignard reagents and organolithiums, normally give ...
direct carbonyl addition on rxn with alpha-beta-unsaturated ketones