Organic Chemistry

1. Organic Chemistry The study of carbon-based compounds and their properties.

2. Organic Chemistry

3. Organic Chemistry

4. Organic Chemistry Historically the distinction between inorganic and organic substances was based on whether or not they were produced by living systems. It was believed that some sort of “life force” was needed to synthesize them.

5. however... NH4OCN  H2N—C—NH2 O urea In 1828, the German chemist Freidrich Wohler (1800-1882) prepared urea from the inorganic salt ammonium cyanate by simple heating.

6. Hydrocarbons: contain only hydrogen and carbon Hydrocarbons can be divided into different types, depending on their bonding. Hydrocarbons Aromatic Aliphatic Alkanes Alkenes Alkynes Cyclic

7. Naming Organic Molecules Alkanes - - Carbon chain, no double or triple bonds. All single bonds Alkenes - - Carbon chain, contains double bond(s) Alkynes - - Carbon chain, contains triple bond(s)

8. Naming Organic Molecules There are two parts to the main name of each molecule… suffix: tells the type of bonding in the chain or ring prefix: tells the # of carbons in main chain or ring

9. Prefix: indicates number of carbon atoms in the main chain or ring • meth- • eth- • prop- • but- • pent- • 6 hex- • 7 hept- • oct- • non- • dec-

10. Suffix: indicates types of bonds present Alkanes: (all single bonds) ___ -ane Alkenes: (double bond) ___ -ene Alkyne: (triple bond) ___ -yne

11. For example…

12. For example…

13. For example…

17. Saturated Hydrocarbons • contain only single C-C bonds

18. Unsaturated hydrocarbons: • contain double or triple C-C bonds

19. Saturated Hydrocarbons: • the ALKANES: chains of carbon connected by single bonds:

20. ALKANESmethane, CH4

21. ALKANESethane, C2H6

22. ALKANESpropane, C3H8

23. ALKANESbutane, C4H10

24. ALKANESpentane, C5H12

25. ALKANEShexane, C6H14

26. ALKANESoctane, C8H18

27. “Normal” v. Branched • “normal” hydrocarbons are straight chains; no branching • Branched-chain hydrocarbons – isomers of “normal” hydrocarbons; have same formula, but different structures

28. n-butane

29. 2-methlypropane

30. n-pentane

31. 2-methylbutane

32. 2,2-dimethylpentane

33. Cycloalkanes

34. cyclopentane

35. Unsaturated Hydrocarbons: ALKENES – contain C-C double bonds2-pentene

36. Unsaturated Hydrocarbons: ALKENES – contain C-C double bonds2,4-hexadiene

37. Unsaturated Hydrocarbons: ALKYNES – contain C-C triple bonds1-butyne

38. Unsaturated Hydrocarbons: ALKYNES – contain C-C triple bonds3-ethyl-1-pentyne

39. Aromatic Hydrocarbons: benzene – the simplest aromatic hydrocarbon; has a symmetrical ring structure

40. Aromatic Hydrocarbons: benzene – can be drawn like this…

41. Derivatives of benzene: 1-ethyl-2-methylbenzene

42. Derivatives of benzene: 1,2-dimethyl-4-propylbenzene

43. Functional Groups Functional groups: special groups of atoms attached to a hydrocarbon skeleton; the most common sites of chemical reactivity.

44. Organic halides: a hydrogen is replaced by a halogenfluoro-, chloro-, bromo-, iodo-2-iodobutane

45. Organic halides: a hydrogen is replaced by a halogenfluoro-, chloro-, bromo-, iodo-2,4-dibromo-1-hexene

46. Organic halides: a hydrogen is replaced by a halogenfluoro-, chloro-, bromo-, iodo-1-bromo-2-chlorobenzene

47. Alcohols & phenols: contain the hydroxyl group (-OH)alcohols: at least 1 H on a hydrocarbon is replaced by OHphenols: at least 1 H on an aromatic ring is replaced by OH2-propanol

48. Alcohols & phenols: contain the hydroxyl group (-OH)alcohols: at least 1 H on a hydrocarbon is replaced by OHphenols: at least 1 H on an aromatic ring is replaced by OH3-methyl-1-butanol

49. Alcohols & phenols: contain the hydroxyl group (-OH)alcohols: at least 1 H on a hydrocarbon is replaced by OHphenols: at least 1 H on an aromatic ring is replaced by OH1,2-butanediol

50. ethers:compounds in which an O atom is bonded to 2 organic groups: -C-O-C-methoxymethane (dimethyl ether)