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Nucleophilic reactions involving enolate anions

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Nucleophilic reactions involving enolate anions Aldehydes, Ketons and other carbonyl compounds having H on -C - in equilibrium (in solution) - Keto-Enol ... – PowerPoint PPT presentation

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Title: Nucleophilic reactions involving enolate anions


1
Nucleophilic reactions involving enolate anions
Aldehydes, Ketons and other carbonyl compounds
having H on a-C -gt in equilibrium (in solution)
-gt Keto-Enol tautomerization
2
Nucleophilic reactions involving enolate anions
3
Nucleophilic reactions involving enolate anions
4
Nucleophilic reactions involving enolate anions
Enolate anion Conjugated base
5
Nucleophilic reactions involving enolate anions
Hydrogen Exchange
Racemization
6
Nucleophilic reactions involving enolate anions
Conjugation
Enol-Form -gt Keto-Form
Progesterone (female sex hormone)
7
Nucleophilic reactions involving enolate anions
Halogenation
8
Nucleophilic reactions involving enolate anions
Alkylation of enolate anion
Enolate anion acting as carbanion nucleophiles in
SN2 reaction
9
Nucleophilic reactions involving enolate anions
Alkylation of enolate anion
Reaction not possible with aryl halides
10
Nucleophilic reactions involving enolate anions
Alkylation of enolate anion
11
Nucleophilic reactions involving enolate anions
Alkylation of enolate anion
12
Nucleophilic reactions involving enolate anions
Addition-dehydration Aldol reaction
Carbonyl compounds reacting as electrophiles -gt
aldol reaction
Aldehydes are better electrophiles than ketons -gt
aldol reaction more favourable with aldehydes
13
Nucleophilic reactions involving enolate anions
Addition-dehydration Aldol reaction
mixed aldol reaction
14
Nucleophilic reactions involving enolate anions
Addition-dehydration Aldol reaction
Product from aldol reaction dehydrates by heating
in acid or base -gt a,ß unsaturated carbonyl
compound
Under basic conditions -gt E1cb (elimination-unimol
ecular-conjugated base)
15
Nucleophilic reactions involving enolate anions
Addition-dehydration Aldol reaction
Intramolecular aldol reaction
16
Nucleophilic reactions involving enolate anions
Other stabilized anions as nucleophiles nitriles
and nitromethane
17
Nucleophilic reactions involving enolate anions
Other stabilized anions as nucleophiles nitriles
and nitromethane
18
Nucleophilic reactions involving enolate anions
Other stabilized anions as nucleophiles nitriles
and nitromethane
19
Nucleophilic reactions involving enolate anions
Enamines as nucleophiles
20
Nucleophilic reactions involving enolate anions
Enamines as nucleophiles
21
Nucleophilic reactions involving enolate anions
Enamines as nucleophiles
22
Nucleophilic reactions involving enolate anions
Enolate anions from carboxylic acid derivates
23
Nucleophilic reactions involving enolate anions
Enolate anions from carboxylic acid derivates
base
More favourable with ketons and aldehydes
24
Nucleophilic reactions involving enolate anions
Enolate anions from carboxylic acid derivates
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