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Mechanistic Study of Carboxylate Ion Reactivity and Keto-Enol Tautomerization in ?-Keto Acid Formation

An investigation into the reactivity of carboxylate ions and keto-enol tautomerization in the formation of ?-keto acids.

Olivia Smith
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Mechanistic Study of Carboxylate Ion Reactivity and Keto-EnolTautomerization in α-Keto Acid FormationSolution:At first the carboxylate ion (as reaction condition is acidic) will accept a proton and willchange into correspondingcarboxylic acid.In the next stepthe hemiacetal oxygen willattack a proton through its electron lone pairand in the process gets protonated.Now electron pair of water molecule attacks thecarbon α to the carboxylic acid groupand simultaneously the C-O σ bond will get broken (to maintain the carbon tetravalency)and its bonding electrons moves to the positively charged oxygen atom.In the next step keto-enol tautomerization will take place. During this process the ketoneis more stable and thus the equilibrium will shift more towards the ketone product (that isat equilibriumamount of ketone will bemore).Now the water molecule will get eliminated (along with the C-O bonding electron pair)from the intermediate obtainedin the last step. Simultaneously the electron lone pair ofthe hydroxyl group will move in(to maintain carbon tetravalency)to form a π-bond.Thiswill result into formation of another carbonyl group with protonated oxygen.Finallytheprotonisattackedbytheelectronlonepairofwatermoleculeandsimultaneously the σ-bond electron willmove on the positively charged oxygen resultingin the formation of diketone molecule.

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Subject
Chemistry

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