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10 Cards in this Set

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Primary amines, RNH2, add to aldehydes and ketones to yield ?
imines, R2C=NR
Secondary amines, R2NH, add similarly to yield....
enamines, R2N-CR=CR2
Imines are important intermediates in?
many metabolic pathways
Imine formation and enamine formation appear different because
one leads to a product with a C=N double bond and the other leads to a product with a C=C double bond
Both Imine and Enamine are typical examples of nucleophilic addition rxns in which .....
water is eliminated from the initially formed tetrahedral intermediate and a new C=Nu double bond is formed
Imines are formed in a process that begins with a ________ ____________nucleophilic addition of the primary amine to the carbonyl group, followed by transfer of a proton from nitrogen to oxygen to yield ?
- reversible, acid-catalyzed


- a neutral amino alcohol, or carbinolamine
Protonation of the carbinolamine oxygen in Imines formation by an acid catalyst then converts the -OH into ________ and E1-like loss of water produces _________ _______. Loss of a proton from nitrogen gives ?
- a better leaving group (-OH2+),

- an iminium ion

- the final product and regenerate the acid catalyst
Imine formation is _______ at both high pH and low pH but reaches a maximum rate at?
- slow

- at a weakly acidic pH around 4 to 5
Rxn of an aldehyde or ketone with a secondary amine, R2NH, rather than a primary amine yields?
an enamine
The process of making an enamine is identical to imine formation ______ ______ _____, but at this point there is noproton on nitrogen that can be lost to form a neutral imine product. The difference is that??
- up to the iminium ion stage

- a proton is lost from the neighboring carbon (the alpha carbon) yielding an enamine