1. Smith, Janice Gorzynski. General, Organic, & Biological Chemistry 2nd Ed. 1 CHAPTER 16 Aldehydes & Ketones General, Organic, & Biological Chemistry Janice Gorzynski Smith

2. CHAPTER 16 Aldehydes & Ketones Smith, Janice Gorzynski. General, Organic, & Biological Chemistry 2nd Ed. 2 Learning Objectives:  Nomenclature for aldehydes & ketones  Identify structure and describe bonding of aldehydes & ketones  Aldehyde oxidation without alcohol oxidation  Addition reactions at C – O double bond  Hemiacetal & acetal formation  Identify cyclic hemiacetals CH 16 Homework: End of Chapter problems: 24, 25, 32, 34, 36, 38, 44, 54, 56, 60, 64, 66, 72, 74, 78, 80, 82, 86, 88, 90, 96

3. Structure Aldehydes & Ketones Smith, Janice Gorzynski. General, Organic, & Biological Chemistry 2nd Ed. 3

4. 4 Structure Aldehydes & Ketones

5. Smith, Janice Gorzynski. General, Organic, & Biological Chemistry 2nd Ed. 5 Ketones Intermolecular Forces

6. Smith, Janice Gorzynski. General, Organic, & Biological Chemistry 2nd Ed. 6 Ketones & Aldehydes Intermolecular Forces

7. Smith, Janice Gorzynski. General, Organic, & Biological Chemistry 2nd Ed. 7 Aldehydes Examples Citral (lemongrass) Cinnamaldehyde (cinnamon bark) Vanillin (vanilla bean)

8. Nomenclature Aldehydes 8 # Greek Root Straight Chain Alkane Name 1meth methane 2eth ethane 3prop propane 4but butane 5pent pentane 6hex hexane 7hept heptane 8oct octane 9non nonane 10dec decane # CarbonsStructure Alkyl Group Name 1CH3-methyl 2CH3CH2-ethyl 3CH3CH2CH2-propyl 4CH3CH2CH2CH2-butyl 5CH3CH2CH2CH2CH2-pentyl 6CH3CH2CH2CH2CH2CH2-hexyl Smith. General Organic & Biolocial Chemistry 2nd Ed. parentsuffixprefix ++ parent suffix First give location and type of substituents. How many carbons in longest chain? Aldehyde @ C1, Ketone @ lowest # C What is the functional group? How many? Aldehyde = -al; Ketone = -one petan 1 2 3 4 5 al 2,4-dimethyl * Note: when we have more then 1 aldehyde or ketone the parent name has an “a” added on: hexa instead of hex O

9. Smith, Janice Gorzynski. General, Organic, & Biological Chemistry 2nd Ed. 9 Ketones Examples Tetracycline: antibiotic Testosterone Progesterone

10. Nomenclature Ketones 10 # CarbonsStructure Alkyl Group Name 1CH3-methyl 2CH3CH2-ethyl 3CH3CH2CH2-propyl 4CH3CH2CH2CH2-butyl 5CH3CH2CH2CH2CH2-pentyl 6CH3CH2CH2CH2CH2CH2-hexyl Smith. General Organic & Biolocial Chemistry 2nd Ed. parentsuffixprefix ++ parent suffix First give location and type of substituents. Then the location of the ketone How many carbons in longest chain? Aldehyde @ C1, Ketone @ lowest # C What is the functional group? How many? Aldehyde = -al; Ketone = -one hexa 1 2 3 4 5 dione 2,4 - * Note: when we have more then 1 aldehyde or ketone the parent name has an “a” added on: hexa instead of hex O 6 O Ketone is C1 in cyclic ketones then number to make the first substituent on the smallest C # Common names for ketones: Name both alkyl groups Order alphabetically Add the work ketone

11. Smith, Janice Gorzynski. General, Organic, & Biological Chemistry 2nd Ed. 11 Aldehydes Oxidation

12. Smith, Janice Gorzynski. General, Organic, & Biological Chemistry 2nd Ed. 12 Aldehydes Selective Oxidation

13. Ketones & Aldehydes Biological Oxidation

14. Ketones & Aldehydes Biological Oxidation

15. Smith, Janice Gorzynski. General, Organic, & Biological Chemistry 2nd Ed. 15 Ketones & Aldehydes Addition Reactions Reduction with H 2 & Catalyst Formation of Acetals Nucleophilic Addition

16. Smith, Janice Gorzynski. General, Organic, & Biological Chemistry 2nd Ed. 16 Ketones & Aldehydes Nucleophilic Addition

17. Smith, Janice Gorzynski. General, Organic, & Biological Chemistry 2nd Ed. 17 Ketones & Aldehydes Reduction

18. Smith, Janice Gorzynski. General, Organic, & Biological Chemistry 2nd Ed. 18 Ketones & Aldehydes Reduction

19. Smith, Janice Gorzynski. General, Organic, & Biological Chemistry 2nd Ed. 19 Ketones & Aldehydes Biological Reduction

20. Smith, Janice Gorzynski. General, Organic, & Biological Chemistry 2nd Ed. 20 Ketones & Aldehydes Acetal Formation

21. Smith, Janice Gorzynski. General, Organic, & Biological Chemistry 2nd Ed. 21 Ketones & Aldehydes Acetal Formation

22. Smith, Janice Gorzynski. General, Organic, & Biological Chemistry 2nd Ed. 22 Ketones & Aldehydes Acetal Formation

23. Smith, Janice Gorzynski. General, Organic, & Biological Chemistry 2nd Ed. 23 Ketones & Aldehydes Acetal Formation

24. Smith, Janice Gorzynski. General, Organic, & Biological Chemistry 2nd Ed. 24 Ketones & Aldehydes Acetal Formation

25. Smith, Janice Gorzynski. General, Organic, & Biological Chemistry 2nd Ed. 25 Ketones & Aldehydes Acetal Hydrolysis