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MCAT Org. Chem Ch. 7

TermDefinition
α-Carbon Carbon adjacent to the carbonyl carbon
α-Hydrogens Hydrogens attached to the α-carbon
α-Hydrogens Are Relatively: Acidic and can be removed by a strong base
The Electron-Withdrawing Oxygen Of The Carbonyl: Weakens the C-H bonds on α-carbons
The Enolate Resulting From Deprotonation Can Be: Stabilized by resonance with the carbonyl
Ketones Are Less Reactive Toward Nucleophiles Because Of: Steric hindrance and α-carbanion destabilization
Reasons For Ketones' Less Reactivity Towards Nucleophilicity The presence of an additional alkyl group crowds the transition step and increases its energy. The alkyl group also donates electron density to the carbanion, making it less stable.
Aldehydes And Ketones Exist In The Traditional: Keto form, C=O, and less in teh enol form (enol = ene + ol = double bond + alcohol)
Tautomers Isomers that can be interconverted by moving a hydrogen and a double bond. The keto and enol forms are tautomers of each other.
The Enol Form Can Be Deprotonated As An: Enolate.
Enolates Are Good: Nucleophiles
In The Michael Addition, An Enolate Attacks: An α, β-unsaturated carbonyl, creating a bond
Kinetic Enolate Is Favored By: Fast, irreversible reactions at lower temperatures with strong, sterically hindered bases
Thermodynamic Enolate Is Favored By: Slower, reversible reactions at higher temps with weaker, smaller bases
Enamines Tautomers of imines. Enamines are the less common tautomer.
In The Aldol Condensation, The Aldehyde Or Ketone Acts: As both nucleophile and electrophile, resulting in the formation of carbon-carbon bond in a new molecule called an aldol
Aldol Contains: Both aldehyde and alcohol functional groups
Nucleophile Of Aldol Condensation Is: The enolate formed from the deprotonation of the α-carbon
Electrophile Of Aldol Condensation Is: The aldehyde or ketone in the form of keto tautomer
Steps Of Aldol Condensation: First, a condensation reaction occurs in which two molecules come together. After the aldol is formed, a dehydration reaction (loss of a water molecule) occurs which results in an α, β-unsaturated carbonyl.
Retro-aldol Reactions Are the reverse of aldol condensations. They result in the bond between an α- and β-carbon being cleaved.
Retro-aldol reactions Are Catalyzed By: Heat and base
Created by: SamB91