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enamine


mechanism


saponification


mechanism
saponification




mechanism


reagents + mechanism


beta-keto ester


beta-keto ester, mechanism
makes ketones


(malonic ester)


mechanism (malonic ester)
malonic ester + saponification




mechanism


Aldol
if you see only one aldehyde or ketone assume it’s 2 eq.


mechanism
if you see alkene next to carbonyl croup = aldol (practice retrosynthesis)


Knoevenagel (EWGs)


mechanism * Knoevenagel




mechanism*
aromaticity


Michael rxn


mechanism* Michael rxn
1,4 addition.
thermodynamic product.
soft nucleophile


Hard nucleophile


mechanism
hard nucleophile




mechanism
1,4 addition


Intra-molecular Aldol


mechanism*
ring size usually 5 or 6 but can be 4 occasionally


crossed aldol


mechanism
if you see alkene next to carbonyl croup = aldol (practice retrosynthesis)




mechanism
if you see alcohol next to carbonyl croup = could be aldol (practice retrosynthesis)




mechanism*
Pka ketone = 19, Pka = 24
(so ketone is nucleophile)
+ makes two ketones


Claisen condensation
(Ester + Ester)


mechanism
Way to make beta-keto ester.
Claisen condensation (Ester + Ester)


Dieckmenn rxn


mechanism
Dieckmenn rxn
easy way to make 5 member rings


Crossed Cleisen


Mechanism
Crossed Cleisen


Robinson annulation


Mechanism*
Robinson annulation
1,4 addition + aldol
if you see alkene next to carbonyl croup = aldol (practice retrosynthesis)


Nazarov cyclization


mechanism***
Nazarov
stereochemistry!!!
