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Organic Chemistry Ch. 7 - Aldehydes and Ketones II
MCAT
8
Organic Chemistry
Undergraduate 2
05/30/2016

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Term
enol form
Definition
contains the carbon carbon double bond
Term
keto form
Definition
contains the carbon oxygen double bond
Term
tautomerization
Definition
interconverting between isomers by moving a hydrogen and a double bond; keto and enol are tautomers of each other
Term
enolate
Definition
deprotonated enol; good nucleophile
Term
Michael addition
Definition

when an enolate attacks an α,β-unsaturated carbonyl, creating a bond

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Term
kinetic and thermodynamic enolates
Definition
the kinetic enolate will form with the less substituted carbon and the thermodynamic enolate will form with the more substituted carbon; same properties for kinetic and thermodynamic products still apply
Term
enamines and imines
Definition

tautomers of each other; the nitrogen double bonded to the carbon in the imine is converted to a double bond between two carbons

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Term
aldol condensation
Definition
  • the aldehyde or ketone acts as both nucelophile and electrophile resulting in the formation of a carbon-carbon bonds in a new molecule called an aldol (contains both aldehyde and alcohol functional groups)
  • the nucleophile is the enolate formed from the deprotonation of the α-carbon
  • the electrophile is the aldehyde or ketone in the form of the keto tautomer
  • First, a condensation reaction occurs in which the two molecules come together
  • After the aldol is formed, a dehydration reaction occurs resulting in an α,β-unsaturated carbonyl

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