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Chemistry of Carbonyl Compounds (McM 19-12) Nucleophilic addition / substitution May also be acid cat.

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Presentation on theme: "Chemistry of Carbonyl Compounds (McM 19-12) Nucleophilic addition / substitution May also be acid cat."— Presentation transcript:

1 Chemistry of Carbonyl Compounds (McM 19-12) Nucleophilic addition / substitution May also be acid cat.

2 The Cannizzarro reaction (McM 19.13) Hydride as leaving group!

3 Conjugate Addition (McM 19.14) 1,2-addition, Ex: Alchohols Organolithium 1,4-addition, Ex: Amines Organocuprates Michael reaction (McM 23.11) Michael acceptor

4 Robinson Annulation (McM 23.13) Ring forming react. annulus (lat.) = ring

5 E:- Alkyl halides - Carbonyl compounds (Aldol, Claissen condens.) - Halides

6 Michael acceptor Enolizable Alkylation of enolate anions (McM 22.8) Ketones, esters, nitriles (Aldehydes: condensation) Base: Strong, sterical hindrance

7 Alkylation of 1,3-dicarbonyl compounds followed by decarboxylation

8 Enamines as enolate equivalents (McM 23.12, Lab ex. 11) Synthesis of enamines (cf McM 19.9)

9 Reactivity of enamines Alkylation (alkyl halides) Conjugate addition (Michael acceptors) Acylation (acid halides) Monoalkylation No strong base

10 Halogenation of enolate anions (McM 22.7)

11 Halogenation of neutral enols (McM 22.3) mainly monohalogenated prod.  -Bromination of acids (McM 22.4)

12 Carbonyl condensations in nature (McM 21.8, 23.14) Acetyl-CoA (Acetyl co-enzyme A) Synthesis of Acetylcholine (neurotransmittor) Acyl-CoA

13

14 Polyesters, polyamides etc (McM 21.9) Acyl subst react Step-Growth polymers (Chain-Growth polymers: Polyenes)


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