Enols and Enolates Flashcards
(21 cards)
1
Q
Crossed aldol addition
A
- NaOH, H2O / 2. Ketone (enolizable), slow
2
Q
Dieckmann Condensation
A
- NaOEt / 2. H3O+
3
Q
Aldol condensation
A
Heat
4
Q
Directed aldol addition
A
- LDA / 2. Ketone / 3. H2O
5
Q
Crossed Directed Claisen
A
- LDA / 2. Ester 3. H3O+
6
Q
Self-Claisen
A
- NaOEt, HOEt (match alkyl group) / 2. H3O+
7
Q
Cuprate Addition
A
- R2CuLi / 2. H3O+
8
Q
Unsymmetric thermodynamic enolate alkylation
A
- NaOMe OR NaOEt OR NaH, 25 deg. / 2. R-X
9
Q
Haloform rxn (α-halogenation of a ketone, basic condit.)
A
X2 / NaOH, H2O
10
Q
Acetoacetic Acid Synthesis
A
a
1. NaOEt, HOEt / 2. R-X / 3. H3O+, heat
11
Q
Aldol addition (one partner)
A
NaOH / H2O
12
Q
Ketone to enol (tautomerization)
A
H3O+ OR NaOH, H2O
13
Q
Symmetric enolate alkylation
A
X-R
14
Q
Crossed Claisen
A
- NaOMe / 2. Ester, slow 3. H3O+
15
Q
HVZ rxn (α-halogenation of carboxylic acid)
A
- Br2, PBr3 / 2. H2O
16
Q
Stork Enamine Reaction
A
- HNR2, TsOH / 2. alpha-beta unsaturated carbonyl / 3. H3O+
17
Q
Unsymmetric kinetic enolate alkylation
A
- LDA, -78 deg. / 2. R-X
18
Q
Michael Reaction
A
- KOH / 2. H3O+
19
Q
Ketone to enolate (100%)
A
LDA OR NaH
20
Q
α-Halogenation of a ketone (acidic condit.)
A
Br2 / H3O+
21
Q
Malonic Ester Synthesis
A
- NaOEt, HOEt / 2. R-X / 3. H3O+, heat
