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1 Nucleophilic reactions involving enolate anions Aldehydes, Ketons and other carbonyl compounds having H on α-C -> in equilibrium (in solution) -> Keto-Enol.

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Presentation on theme: "1 Nucleophilic reactions involving enolate anions Aldehydes, Ketons and other carbonyl compounds having H on α-C -> in equilibrium (in solution) -> Keto-Enol."— Presentation transcript:

1 1 Nucleophilic reactions involving enolate anions Aldehydes, Ketons and other carbonyl compounds having H on α-C -> in equilibrium (in solution) -> Keto-Enol tautomerization

2 2 Nucleophilic reactions involving enolate anions

3 3

4 4 Enolate anion Conjugated base

5 5 Nucleophilic reactions involving enolate anions Hydrogen Exchange Racemization

6 6 Nucleophilic reactions involving enolate anions Conjugation Enol-Form -> Keto-Form Progesterone (female sex hormone)

7 7 Nucleophilic reactions involving enolate anions Halogenation

8 8 Nucleophilic reactions involving enolate anions Alkylation of enolate anion Enolate anion acting as carbanion nucleophiles in S N 2 reaction

9 9 Nucleophilic reactions involving enolate anions Alkylation of enolate anion Reaction not possible with aryl halides

10 10 Nucleophilic reactions involving enolate anions Alkylation of enolate anion

11 11 Nucleophilic reactions involving enolate anions Alkylation of enolate anion

12 12 Nucleophilic reactions involving enolate anions Addition-dehydration: Aldol reaction Carbonyl compounds reacting as electrophiles -> aldol reaction Aldehydes are better electrophiles than ketons -> aldol reaction more favourable with aldehydes

13 13 Nucleophilic reactions involving enolate anions Addition-dehydration: Aldol reaction mixed aldol reaction

14 14 Nucleophilic reactions involving enolate anions Addition-dehydration: Aldol reaction Product from aldol reaction dehydrates by heating in acid or base -> α,β unsaturated carbonyl compound Under basic conditions -> E1cb (elimination-unimolecular-conjugated base)

15 15 Nucleophilic reactions involving enolate anions Addition-dehydration: Aldol reaction Intramolecular aldol reaction

16 16 Nucleophilic reactions involving enolate anions Other stabilized anions as nucleophiles: nitriles and nitromethane

17 17 Nucleophilic reactions involving enolate anions Other stabilized anions as nucleophiles: nitriles and nitromethane

18 18 Nucleophilic reactions involving enolate anions Other stabilized anions as nucleophiles: nitriles and nitromethane

19 19 Nucleophilic reactions involving enolate anions Enamines as nucleophiles

20 20 Nucleophilic reactions involving enolate anions Enamines as nucleophiles

21 21 Nucleophilic reactions involving enolate anions Enamines as nucleophiles

22 22 Nucleophilic reactions involving enolate anions Enolate anions from carboxylic acid derivates

23 23 Nucleophilic reactions involving enolate anions Enolate anions from carboxylic acid derivates base More favourable with ketons and aldehydes

24 24 Nucleophilic reactions involving enolate anions Enolate anions from carboxylic acid derivates

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