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Organic Chemistry Archive

Multicomponent Reactions

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Malonic Ester Synthesis – Alkylation of Enolates

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Basic conditions force ester hydrolysis and yield carboxylates.

Acetoacetic Ester Synthesis – Alkylation of Enolates

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Using the non-selective nature of acetoacetic ester synthesis and malonic ester synthesis to produce cyclic compounds

Using the non-selective nature of acetoacetic ester synthesis and malonic ester synthesis to produce cyclic compounds

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In the presence of a base alpha-hydrogens to carbonyl functional group can be abstracted very easily to yield a carbanion

Chemistry of Enolates and Enols – Acidity of Alpha-Hydrogens

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Sulfonated Bathophenanthroline, TBTA and Amineriazole

Catalytic Azide-Alkyne Cycloaddition: Reactivity and Application

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C-alkylation vs O-alkylation - A continuous challenge in the chemistry of enolates.

Chemistry of Enolates – C vs O Alkylation

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Figure 2 - Energy profile diagram of thermodynamic product vs kinetic product

Thermodynamic Product vs Kinetic Product – with example of enolate formation of 2-methylcyclohexanone

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C-alkylation of phenolate

Phenolates- O-alkylation and C-alkylation

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Figure 1 - Reaction of carbonyl containing compound with amine yields imine and enamine

Imines and Enamines – Nitrogen Analogs of Enols and Enolates

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Reaction at the less reactive 6-position of 2-methyl cyclohexanone is forced due to formation of enamine

Producing and Using Imines and Enamines

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Michal Addition with a michael acceptor and a michael donor - examples of reactants

Michael Addition

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Base catalyzed dehydration of aldol or ketol leading to alpha,beta-unsaturated carbonyl compound.

Aldol Condensation – Base Catalyzed

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Aldol condensation - leading to aldol or ketol which can undergo dehydration to produce the alpha,beta-unsaturated aldehyde or ketone

Aldol Condensation – Acid Catalyzed

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Formation of a cyclic transition state during enolate formation which controls formation of E-enol or Z-enol

Directed Aldol Synthesis: Part 1 – Formation of E-Enolate and Z-Enolate

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How the E-enolate selectively produce anti-product in order to obtain directed aldol synthesis.

Directed Aldol Synthesis: Part 2 – Syn and Anti control using Zimmerman Traxler principle

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Synthesis of Boron Enolates for Aldol Condensation

Boron Enolates for Aldol Synthesis and Other Reactions

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pKa scale for acidity and basicity

Henderson–Hasselbalch Equation: Derivation of pKa and pKb

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Thin Layer Chromatography (TLC): Principle (with Animation)

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Principle of Reversed-Phase Chromatography HPLC/UPLC (with Animation)

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