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Organic chemistry for medicine and biology students Organic B Chapter 18 Aldehydes and Ketones

Organic chemistry for medicine and biology students Organic B Chapter 18 Aldehydes and Ketones By Prof. Dr. Adel M. Awadallah Islamic University of Gaza. Nomenclature of Aldehydes and Ketones. Common aldehydes. Common Ketones. Nomenclature of aldehydes and ketones.

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Organic chemistry for medicine and biology students Organic B Chapter 18 Aldehydes and Ketones

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  1. Organic chemistry for medicine and biology students Organic B Chapter 18 Aldehydes and Ketones By Prof. Dr. Adel M. Awadallah Islamic University of Gaza

  2. Nomenclature of Aldehydes and Ketones Common aldehydes

  3. Common Ketones

  4. Nomenclature of aldehydes and ketones (al) aldehyde, (one) ketone alkanes < alkenes < OH < ketone < aldehyde < acid < ester Examples

  5. Acyl groups

  6. Common aldehydes and ketones

  7. Synthesis of aldehydes and Ketones • Oxidation of Alcohols primary gives aldehydes using PCC secondary gives ketones 2) Friedel-Crafts 3) From Alkynes

  8. 4- Aldehydes from Acid Chlorides

  9. 5- Ketones from Acid Chlorides

  10. Synthesis of Alkylbenzenes

  11. Reduction of Acids and their derivatives by Lithium Aluminum hydride (LAH)

  12. Naturally occuring aldehydes and Ketones

  13. The carbonyl group

  14. Reactions of the carbonyl group

  15. Remember: Generation of a chiral center

  16. A. Hydration and Hemiacetal Formation • Water adds rapidly to the carbonyl function of aldehydes and ketones. In most cases the resulting hydrate (a geminal-diol) is unstable relative to the reactants and cannot be isolated. • Exceptions to this rule exist, • one being formaldehyde (a gas in its pure monomeric state). • Thus, a solution of formaldehyde in water (formalin) is almost exclusively the hydrate, or polymers of the hydrate. • Another is chloral hydrate

  17. Addition of Alcohols

  18. Examples

  19. Addition of hydrogen cyanide to aldehydes and ketones

  20. Reducing Agents The reduction of an aldehyde You get exactly the same organic product whether you use lithium tetrahydridoaluminate or sodium tetrahydridoborate. For example, with ethanal you get ethanol:

  21. The reduction of a ketone • Again the product is the same whichever of the two reducing agents you use. • For example, with propanone you get propan-2-ol: • Reduction of a ketone leads to a secondary alcohol.

  22. REACTION OF ALDEHYDES AND KETONES WITH GRIGNARD REAGENTS

  23. The reaction between Grignard reagents and methanal The reaction between Grignard reagents and other aldehydes The reaction between Grignard reagents and ketones

  24. Reaction with Acetylides

  25. OXIDATION OF ALDEHYDES AND KETONES

  26. Cannizzaro reaction. (self oxidation/reduction) • a reaction ofaldehydes without α-hydrogens The Cannizzaro reaction, named after its discoverer Stanislao Cannizzaro, is a chemical reaction that involves the base-induced disproportionation of an aldehyde.[1][2] Cannizzaro first accomplished this transformation in 1853, when he obtained benzyl alcohol and potassium benzoate from the treatment of benzaldehyde with potash (potassium carbonate). More typically, the reaction would be conducted with sodium or potassium hydroxide:

  27. Mechanism of the Cannizzaro Reaction

  28. Crossed Cannizzaro: Formaldehyde is the most easily oxidized aldehyde. When mixed with another aldehyde that doesn’t have any alpha-hydrogens and conc. NaOH, all of the formaldehyde is oxidized and all of the other aldehyde is reduced.

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