enolates and tautomerisation Flashcards
tautomer
atoms arranged differently
when does tautomerisation occur
when there is an H on the alpha carbon on a carbonyl
how are ketos and enols related
are tautomers of each other
what is the attacking species in tautomerisation
a base
in which conditions will the base attack the alpha proton first
basic
what is formed in acidic conditions of tautomerisation
enol
what is formed in basic conditions of tautomerisation
enolate
what makes the H acidic
the electrophilic C=O allow INDUCTIVE effects from the H, making it more acidic
is an oxyanion more or less stable than a carboanion
more stable as the O is more able to stabilise the -ve charge than the C in the carboanion.
are enolates electrophilic or nucleophilic
nucleophilic
how do enolates react
through the C of the C=C
what types of tautomer reactions can occur
halogenation, Aldol reactions (nucleophilic enolate and electrophilic benzene ring)
what does nature use aldol reactions for
making sugars
