2009 4 Carbonyl Chemistry REv N CN - Reversible Additions...

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Reversible Additions to Carbonyls 3a . Imines (Biological Reactions) 3b . Enamines 4 . Cyanohydrins (Biodefence weapon ) Lecture 4 2009
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Top 12 reactions 1. 1,1- halo hydrin formation 2. a) Hydration b) Acetal formation 3. a) Imine formation 8. a) O xidation with Jones Reagent (Aldehydes) b) Bayer-Villiger o xidation (Ketones) b) En amine formation 4. Cya n ohydrin formation 5. Grignard Addition 6. Wittig Reaction 7. Reduction 9. Deuterium exchange 10. α - Halogen ation 11. α -alkylation 12. Ald ol formation
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Rxns 1- 7 are Nucleophilic Additions to Carbonyl R -C= O H : nu Halides ( Cl - ) Oxygen (H 2 O , R O H) Nitrogen (1 ° , 2 ° , 3 ° amines ) Carbon (-C N, Grignard, Wittig) Hydrogen (hydride) (NaBH 4 , LiAlH 4 )
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Assignment 1 (McMurry 6e) Topic Chapter Section Problems Preview p.672 - 681 II, III p. 674-676 Nomenclature 19.1 19.1, 19.2 Nucleophilic addition 19.4, 19.5 19.6 Hydration 19.6 19.7, 19.8 Acetal Formation 19.11 19.14,19.15,19.38 Imine/Enamine 19.9 19.10, 19.11 Cyanohydrins 19.7 19.9 Grignard Addition 19.8 17.10 Wittig 19.12 19.16, 19.49 Hydride Reduction 19.8 19.71 Oxidation 17.8,19.3
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Assignment 1 (McMurry 7e) Topic Chapter Section Problems Preview p.688 - 694 II, III p. 688-690 Nomenclature 19.1 19.1, 19.2 Nucleophilic addition 19.4, 19.5 19.6 Hydration 19.5 19.7, 19.8 Acetal Formation 19.10 19.14,19.15,19.39 Imine/Enamine 19.8 19.10, 19.11 Cyanohydrins 19.6 19.9 Grignard Addition 19.7 17.10 Wittig 19.11,19.12 19.16, 19.17, 19.51 Hydride Reduction 19.8,19.12 19.73 Oxidation 17.7,19.3
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3a,b Nucleophilic attack by nitrogen nucleophiles H C H O N H + O .. H C H N + + H 3 H 2 H . . Simplest case Note: Most simple imines decompose in water to give the parent carbonyl group. Carbonyl group is the thermodynamic resting place Aldimine Imino group Aldehyde Carbonyl group
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with Primary Amines (R = alkyl) and ammonia (R = H). H
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This note was uploaded on 07/28/2009 for the course ORGANIC CH CHEM 2204 taught by Professor Dr.levin during the Winter '08 term at Indian Institute of Technology, Chennai.

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2009 4 Carbonyl Chemistry REv N CN - Reversible Additions...

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