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CHAPTERͲ12

MECHANISMOFREACTION

ALDOLCONDENSATION:

Analdolcondensationisanorganic

hydroxyaldehyde providing agoodwaytoformcarbon-carbonbonds. important condensationsarealsocommonly analdehydetoform molecules andpharmaceuticals. smallmolecule. called

ClaisenͲSchmidtcondensation.

MECHANISM:

a dehydration - aneliminationreaction.Dehydrationmaybe accompanied bydecarboxylationwhenanactivatedcarboxyl groupispresent. acid

Ͳcatalyzedenolmechanism.

TYPESOFCONDENSATIONS

other additionreactionstocarbonylcompounds.

Whenthebaseisanamineandtheactivehydrogen

a

Knoevenagelcondensation.

generatedfromananhydride. thesamemoleculeandyieldsacyclicmolecule compound. a carbonylgroup,whichfirstengageinaMichael reactionpriortothealdolcondensation.

CLAISENCONDENSATION

occursbetweentwoestersoroneesterand another reactionin1881.

TYPES:

esterisused. groups this memberedc.

MECHANISM

In which resonanceͲstabilizedenolateanion. present. isolated.Notethatthereactionrequires a otherwiseendergonicreaction.

Thatis,Claisencondensationdoesnotwork

thelaststep.

CANNIZZAROREACTION

TheCannizzaroreaction,namedafterits

disproportionationinexcellentyields. formaldehydeasreducingagent.

Application:

centers.

30%base.

[5]

Toavoidthelowyields,itismorecommonto

conduct aldehyde. ,which is oxidizedtosodiumformate andthecorrespondingalcoholis isstilllow. in a mortarand pestle.

CROSSEDALDOLCONDENSATION

Crossed

example:

Mechanism

Step aldehydereversibly. Step more accessiblecarbonylcarbon. Step

3:Alkoxideion2isprotonatedbywater.

Step ion. Step

5:Enolateion4losesahydroxideion.

elimination viaE1cBmechanism.Thus,crossedaldol elimination.

Crossed

cannizzaroreaction: is E.g. alkali. electrondonatinggroupsonit. reductionofsomealdehydes. acids byanintermolecularCannizzaroreaction. E.g.

HydroxyͲ2Ͳphenylethanoicacid)

reaction bygiving(oͲhydroxymethyl)benzoicacid.

BENZOINCONDENSATION

first aldehydes.

MechanismofBenzoinCondensation

inthisreaction.

CͲatom:

elimination attheendofthereaction:

PERKINCONDENSATION

Henry unsaturatedaromaticacidbythealdol presenceofanalkalisaltoftheacid. acid reactiontype.

Reaction

mechanism other grouptransfer

Knoevenagelcondensation

thealdolcondensation. a betaconjugatedenone.

APPLICATION

acid enone3isachargetransfercomplexmolecule. production ofCoartem) eventuallybeobtained. condensationisdemonstratedinthisMORE triazole

REFORMATSKYREACTION

TheReformatskyreactionisanorganic

1,withɲͲhaloesters,

Mechanism

oftheReformatskyReaction additiontogiveɴͲhydroxyesters. availablecommercially.

WITTIGREACTION

MICHAEL

ADDITION

themildformationofCͲCbonds. [4]

Manyasymmetricvariants

exist. ketoesters, product nucleophile its three solvent)bytheenolate4to5isthefinalstep. carbon polarized (soft carbon bond.Thisalsotransferstheenolateto enolizable; however,onemaytakeadvantageofthenew locusquotesdbs_dbs50.pdfusesText_50