acetoacetic ester synthesis
method for ketone preparation in which alkylation of the enolate of ethyl acetoacetate is followed by reaction with H3O+ and heat to decarboxylate the acetic ester
addition reaction
reaction in which two or more reactants combine to form products
aldol
molecule formed from the reaction of an enolate with a carbonyl, composed of a carbonyl and an alcohol
aldol addition reaction
reaction in which aldehydes and/or ketones are treated with a base to yield a solution containing a carbonyl compound and its enolate, which combine through the formation of a bond
aldol condensation reaction
aldol addition wherein the beta-hydroxy aldehyde or ketone dehydrates
alkylation
reaction in which an alkyl group is transferred from one molecule to another organic compound
alpha,beta-unsaturated molecule
molecule with a pi bond between the alpha () and beta () carbons attached to a carbonyl group
Claisen condensation
formation of a beta-keto ester from an ester and a base
condensation reaction
chemical reaction that combines two molecules together with the elimination of a water molecule
conjugate addition
reaction in which a nucleophile reacts with an alpha,beta-unsaturated carbonyl compound in the beta position
decarboxylation
removal of a carboxylic acid (as a CO2 group) by the addition of heat
directed aldol reaction
reaction in which the enolate is prepared in the first step and the intended reactant is added in the second step to ensure the desired product
directed Claisen condensation
reaction in which an ester is treated with lithium diisopropylamide (LDA) or another strong base, followed by the addition of a second ester
enamine
amino group containing the double bond linkage
enolate
anion formed when an alpha hydrogen in the molecule of an aldehyde or a ketone is removed as a hydrogen ion
haloform reaction
cleavage of a methyl ketone by Br2, Cl2, or I2 to form CHX3 (where X is Br, Cl, or I)
halogenation
reaction in which a hydrogen is replaced by a halogen
Hell-Volhard-Zelinsky (HVZ) halogenation reaction
halogenation of a carboxylic acid catalyzed by phosphorus trihalide
intramolecular aldol reaction
reaction in which the enolate and carbonyl components are parts of a single molecule
intramolecular Claisen condensation
reaction in which an ester is deprotonated at the alpha carbon, generating an enolate, which undergoes an intramolecular nucleophilic attack, yielding a cyclic enol. The enol is protonated with an acid to re-form the beta-keto ester.
malonic ester synthesis
preparation of a carboxylic acid by alkylation of the enolate of diethyl malonate
Michael reaction
1,4-addition reaction in which a carbanion is added to an alpha,beta-unsaturated carbonyl compound
practical crossed aldol reaction
reaction in which two different carbonyl compounds are mixed together and only one can form an enolate, preventing self-condensation of the other compound
practical crossed Claisen condensation
ester or ketone enolate mixed with an ester that cannot form an enolate
retro-aldol reaction
reverse of an aldol reaction. It decomposes a beta-hydroxy carbonyl into an aldehyde or ketone and another carbonyl compound.
Robinson annulation
reaction in which a Michael reaction is followed by an intramolecular aldol condensation to form a cyclohexenone ring
Stork enamine reaction
reaction in which ketones are alkylated or acylated through intermediate enamines