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Aldehydes and Ketones

Aldehydes and Ketones. Structure. Structure. Nomenclature of aldehydes. Aldehydes are named by adding the suffix - al to the name of the corresponding hydrocarbon. The carbonyl carbon is given the number 1 . ethanal acetaldehyde. Nomenclature of aldehydes. Nomenclature of aldehydes.

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Aldehydes and Ketones

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  1. Aldehydes and Ketones

  2. Structure

  3. Structure

  4. Nomenclature of aldehydes Aldehydes are named by adding the suffix -alto the name of the corresponding hydrocarbon. The carbonyl carbon is given the number 1. ethanal acetaldehyde

  5. Nomenclature of aldehydes

  6. Nomenclature of aldehydes When -CHO is attached to a ring, the suffix carbaldehyde is used. benzenecarbaldehyde benzaldehyde 3-methylpentanal

  7. Nomenclature of aldehydes

  8. Nomenclature of ketones Ketones are named using the name of the corresponding hydrocarbon followed by the suffix -one. The position of the carbonyl carbon must be indicated. propanone acetone dimethyl ketone One can also name the two radicals, R and R’, followed by the word ketone.

  9. Nomenclature of ketones ethyl methyl ketone 1-phenyl-2-propanone benzyl methyl ketone

  10. Nomenclature of ketones diphenylmethanone benzophenone phenylethanone acetophenone

  11. Nomenclature of ketones

  12. Synthesis of aldehydes - oxidation of primary alcohols PCC = pyridinium chlorochromate

  13. Rosemund reduction RCHO or ArCHO A special catalyst is used: palladium on barium sulfate which has been deactivated (poisoned) with an amine such as quinoline.

  14. Lithium tri-tert-butoxyaluminium hydride

  15. Synthesis of ketones - oxidation of secondary alcohols

  16. Synthesis of ketones - oxidation of secondary alcohols

  17. Synthesis of ketones – hydration of alkynes

  18. Keto - enol tautomerism Structural isomers that are formally related only by the shift of a hydrogen and one or more  bonds are called tautomers.

  19. Friedel-Crafts acylation

  20. Reaction of acid chlorides with dialkylcuprates

  21. Oxidation of aldehydes RCO2H or ArCO2H

  22. Tollens’ test colorless solution silver mirror

  23. Oxidation of ketones - the haloform reaction

  24. Reactivity of the carbonyl group

  25. Nucleophilic addition

  26. Nucleophilic addition - acid catalysis

  27. Addition of cyanide cyanohydrin

  28. Addition of cyanide

  29. Addition of cyanide

  30. Addition of Grignard reagents

  31. Reduction to alcohols

  32. Reduction to alcohols

  33. Reduction to alcohols hydride transfer

  34. Addition of ammonia derivatives

  35. Addition of ammonia derivatives

  36. Addition of ammonia derivatives

  37. Addition of ammonia derivatives

  38. Addition of ammonia derivatives

  39. Reduction to hydrocarbons Zn(Hg), conc. HCl Clemmensen reduction Wolff-Kishner reduction

  40. Reduction to hydrocarbons an antiseptic

  41. Addition of alcohols

  42. Addition of alcohols - hemiacetal formation

  43. Acetal formation

  44. Reactions of acetals H + H + H O 2ROH + R'-C=O 'R C OR 2 OR H

  45. Acetals as protecting groups

  46. Wittig reaction + (C6H5)3PO triphenylphosphine oxide an ylid Georg Wittig, University of Heidelberg, Nobel Prize 1979

  47. Wittig reaction - ylid formation alkyltriphenylphosphonium halide triphenylphosphine an ylid

  48. Wittig reaction

  49. Cannizzaro reaction

  50. Cannizzaro reaction

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