Lecture 3B - Carbonyls and Enol (Enolate) Reactions ....

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Unformatted text preview: Carbonyls and Enol (Enolate) Reactions . euterium xchange 9. Deuterium exchange 10. - Halogen ation 11. -alkylation 12. Ald ol formation Lecture 3A Top 12 reactions of Aldehydes and Ketones 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. - Halogen ation 11. -alkylation 12. Ald ol formation Reactions 9-12 involve Electrophilic attack on Enols /Enolates of Aldehydes or Ketones O H H H O H H H Enol Intermediate 1 multistep O H H E H + E + O H H H O H H E 2 Net Result: Replaced H by E Reactions 9-12 involve Electrophilic attack on Enols/ Enolates of Aldehydes or Ketones O H H H- H + O H H Enolate Intermediate 1 Strong Base O H H E E + O H H 2 Reminder: We can draw an enolate anion in two ways: O O CH 2- Lets talk about how enols are formed Keto Enol Tautomerization O H H H O H H H multistep Enol Ketones (or Aldehydes) and the corresponding Enols are Tautomers : Molecules that are interconvertible by rearrangement of atoms. Tautomers are a special kind of Structural Isomer (same molecular formula but different bond connectivity) Ketone Not all ketones and aldehydes can enolize! Chloral Benzophenone 2,2,6,6- Tetramethylcyclohexanone O H OH For simple ketones (aldehydes), equilibrium favours the carbonyl form over the enol form ....
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Lecture 3B - Carbonyls and Enol (Enolate) Reactions ....

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