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CARBON-CARBON BOND CONSTRUCTION, SELECTIVITY & COMPETITION:…
CARBON-CARBON BOND CONSTRUCTION
SELECTIVITY & COMPETITION: consequences of enolate formation.
REGIOSELECTIVITY: ASYMMETRICAL KETONES
which alpha-side reacts? (kinetic vs. thermodynamic enolates).
CROSSED REACTIONS: Crossed-Aldol and Crossed-Claisen. controlling reaction mixtures to yield a single desired product
reagent: Aldehyde or ketoneCROSS-ALDOL:
nucleophile: Aldehyde or ketone enolate
C=O to C--OH (no leaving group)
product: BETA-HYDROXY carbonyl or
ALPHA_BETA UNSATURATED carbonyl
CROSS-CLAIDEN:
reagent: Ester + (ester, aldehyde, or ketone)
Nucleophile: ester or ketone enolate
leaving group: Alkoxide (OR-)
product: BETA KETO ESTER or BETA DICARBONYL
RING FORMATION
CYCLOHEXENE
CHAIN ELONGATION
ENOLATE: Link alkyl groups of carbonyl fragments
ALDOL
MALONIC ESTER SYNTHESIS
CLAISEN
CARBONYL ELECTROPHILES
ELONATE ATTACKS:
1.CARBONYL (in Claisen & Aldol)
ALKYL HALIDES (in Malonic Ester synthesis)
ALPHA-HYDROGEN ACIDITY
DEPROTONATION next to carbonyl group (in Claisen, Aldol, Malonic Ester syn. Knoevenagel & Alpha-addition
NUCLEOHPILIC CARBANIONS
deprotonation creates
an ELONATE or CARBANION
that acts as a STRONG NUCLEOPHILE
DIENOPHILES
In Diels-Alder: act as
ELECTRON-DEFICIENT ALKENES
CONJUGATE ADDITIONS:
in apha-beta reactions:
act as electrophiles for nucleophilic attack
BLUEPRINT:
Conjugated Systems and Resonance