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tautomerization (a)
H3O+

tautomerization (b)
KOH, H2O

aldol addition
KOH/H2O, 0˚C

aldol condensation
KOH/H2O, heat

kinetic alkylation of ketones
1. LDA, -78 ˚C
2. R-X

thermodynamic alkylation of ketones
1. NaNH2, -78 ˚C or LDA, 40 ˚C
2. R-X

alkylation of aldehydes
1. 2˚ amine
2. R-X
3. H3O+

halogenation of aldehydes and ketones (a)
Br2 (or Cl2), AcOH

halogenation of aldehydes and ketones (b)
Br2 (or Cl2), KOH

conjugate addition (1-2 and 1-4)
1. EtMgBr
2. H3O+

michael addition
1. LDA
2. H3O+

robinson annulation
NaOEt, heat or 1. KOH/H2O 2. H3O+

mannich reaction
1. amine, H+
2. KOH

claisen condensation
1. NaOR (OR matches ester)
2. H3O+

decarboxylation
1. NaOH
2. H3O+, heat

conjugate addition (1-2)
1. EtLi
2. H3O+

conjugate addition (1-4)
1. Et2CuLi
2. H3O+