Kaplan Organic Chemistry: Chapter 7 Aldehydes and Ketones II Flashcards
Are aldehydes/ketones mildly basic or acidic
acidic
aldehydes and ketones can undergo ____, allowing for addition reactions
tauteromerization
tautomer or imine
enamine
in a michael addition, a ___ deprotonates an alpha carbon, making it a good nucleophile. Then, the carbanion attacks the double bond, resulting in an addition AT THE BETA SITE OF THE DOUBLE BOND
a BASE.
what is an aldol
a molecule that contains both an aldehyde and an alcohol.
reactants of an aldol condensation
an aldehyde and a BASE, then an acid workup to form an ALDOL.
afterwards, the aldol is DEHYDRATED to form form an aldehyde with a double bond on the alpha carbon. water is a byproduct.
in a retro aldol reaction, ___ and heat is required to break bonds between alpha and beta carbons to form a ___ and a ____
in a retro aldol reaction, BASE and heat is required to break bonds between alpha and beta carbons to form a KETONE and an ALDEHYDE
____ products form the fastest.
kinetic products
kinetic products contain terminal ___ ___ and the reaction is ____
kinetic products contain terminal DOUBLE BONDS and the reaction is IRREVERSIBLE.
Thermodynamic products form at higher temperatures.
2 steps of aldol condensation
1) aldol addition: adding two aldehydes or an aldehyde and ketone together via basic addition, yielding an ALDOL (aldehyde with alcohol) ( b-hydroxyketone.)
2) dehydration: resulting in an aldehyde with a double bond at the alpha carbon.
aldol condensation is also known as
robinson annulation
an α,b-unsaturated ketone acts as both an ____ (in a Michael addition) and a ____ ( in an intramolecular aldol condensation
α,b-unsaturated ketone as both an electrophile (Michael addition) and a nucleophile (intramolecular aldol condensation
