ORGANIC CHEMISTRY

1. Campbell and Reece Chapter 4 ORGANIC CHEMISTRY

2. Organic Chemistry • study of carbon compounds (most also have hydrogen) • range from small molecules (methane has 4 atoms) to very large one (proteins can have thousands of atoms)

3. Major Elements of Life • Carbon • Hydrogen • Oxygen • Nitrogen • Sulfur • Phosphorus

4. Carbon is very Versatile • because C can form 4 covalent bonds these 6 elements can form an almost limitless # organic molecules

6. VITALISM • Some credit Hippocrates • Simply stated: there is a life force outside physical & chemical laws

7. JonsJakob Berzelius • Swedish chemist in early 1800’s • “Organic compounds come from living things” (only ) • so inorganic compounds found only in nonliving things

8. FredrichWÖhler • German chemist • 1828: synthesized urea in lab (normally made in kidney) • Did not convince Vitalists because he 1 reactant he used came from animal blood

9. Urea

10. Hermann Kolbe • Student of Wohler • Synthesized urea using only inorganic reactants….. • Crushed Vitalism…..sorry Yoda

11. Origin of Life on Earth • Stanley Miller, 1953 • Designed experiment trying to re-create conditions on early Earth • Hypothesized : abiotic synthesis of organic compounds possible

12. Miller’s Experiment • Closed system • Flask of water (early seas) heated • Water vapor rose to another higher chamber containing “atmosphere” • Sparks added (lightening) • “rain” formed, cooled  material collected analyzed

13. Miller’s Experiment

14. Miller’s Conclusion • Complex organic compounds could form spontaneously under conditions thought to exist on early Earth

15. Miller’s Results • 2008: re-analyzed some samples from Miller’s experiments in the 1950’s • Additional organic compounds identified

16. Organic Chemistry • Definition changed to: • Study of Carbon Compounds (regardless of origin)

18. Bonding with Carbon • C has 4 valence e- • Bonds possible: • 4 single covalent bonds • 2 single & 1 double covalent bond • 2 double covalent bonds • 1 single & 1 triple covalent bond

19. Bonding with Carbon

20. Carbon Skeletons • Carbon chains form the backbone of most organic molecules • These skeletons can be • Straight • Branched

21. Carbon Skeleton Variation • In rings:

23. Carbon Skeleton Variation • 1 important source of molecular complexity & diversity that characterizes living organisms

24. Hydrocarbons • C & H • Major components of petroleum products (fossil fuels) • When organism dies all water soluble compounds wash away as it decays. • Fats stay behind  hydrocarbons • Burn fossil fuels because they release a large amount of energy

25. Fossil Fuels

26. Isomers • Cpds with same # and types of atoms but they are arranged differently • Different structures behave differently • 3 types: • Structural Isomers • Cis/trans Isomers • enantiomers

27. Structural Isomers • Differ in covalent arrangements of their atoms • Molecular formula same, structure different

28. Structural Isomers • # possibilities for different arrangements of atoms increases dramatically as carbon skeleton increases in size

29. Cis-trans Isomers • aka geometric isomers • Carbons have covalent bonds with same atoms but these atoms differ in their spatial relationship

30. Cis-trans Isomers • In cis groups are on same side of Carbon • In trans groups are across from each other

31. Cis-trans Isomers • The difference in cis-trans can dramatically affect the biological behavior of the molecule

32. Enantiomers • Isomers that are mirror images of each other • Differ in shape due to having asymmetric carbon

33. Enantiomers • Usually only 1 is biologically active • Other 1 may have much milder effect

35. Functional Groups • Portion of molecule that participates in chemical reactions in a characteristic way • 7 common, & very important functional groups in organic chemistry

36. HYDROXYL-OH • Make alcohols • Properties: • Polar • Can for H-Bonds with water (help cpd dissolve in water)

37. CARBONYL-C=O • Makes: • Ketones: if in middle of molecule • Aldehyde: if at end of molecule • Properties: • can be isomers • ketoses/aldoses

39. CARBOXYL-COOH • Makes: organic acids • Properties: • Can donate H+  COO- • Mostly found in cells in ionized form (charge of -1) & called a carboxylate ion • In amino acids

40. CARBOXYL

41. AMINO-NH2 • Makes: Amines • Properties: • Acts as a base (can take H+) • Found in cells in ionized form with +1 charge • in amino acids

42. AMINE

43. SULFHYDRYL-SH • Makes: thiols • Properties: • 2 –SH can react forming disulfide bridges • These bridges make hair curly

45. PHOSPHATE-PO4 • Structure: • 2 O have (-) charge • Makes: • Organic phosphates • Properties: • Makes molecule polar (-1) charge when in middle, (-2) when on end • Can react with water  energy

46. PHOSPHATE

47. METHYL-CH3 • Makes: • Methylated compounds • Properties: • When attached to DNA, affects expression of genes • Attachment to Testosterone changes biological effect compared to Estrogen (without methyl group)

48. METHYL

49. ADENOSINE TRIPHOSPHATEATP • Made of adenosine + 3 phosphate groups • When 3 phosphates in series, easy to remove 3rd group with water

50. Hydrolysis of ATP