1. Chapter 22 Organic chemistry

2.  chemical compounds consisting primarily of carbon carbon  original definition came from the misperception that these compounds were always related to life processes life

3. Structure of carbon  1s 2 2s 2 2p 2  4 valence electrons (2s 2 2p 2 )  Strong tendency to share electrons  Strong tendency to form covalent bonds

4. Molecular Architecture  4 covalent bonds  tetrahedron  tetrahedron

5.  Strong tendency to form covalent bonds w/ H, O, N, S, P, and halogens

6. Molecular Diversity  Also bond to other carbons to form chains, rings, plates, networks

7. Forms of carbon 1.Diamond  Hardest known material  High density (3.514 g/ cm 3 )  High mp (3550 deg. C)

8. 2.Graphite  Soft  Conducts electricity  High mp (3570 deg. C)  Used as a lubricant, “lead” pencils

9. 3.Coal  Black, rock-like  Burns readily

10. 4.Coke  Made by heating coal  Used for making steel

11. 5. Charcoal

12. Carbon Compounds  Over 4 million known cmpds., natural and synthetic  Almost limitless # of possible structures

13. Can form isomers  Compounds w/ same formula but different structures

14. Hydrocarbons  Compounds of hydrogen and carbon

15. 1. Alkanes  Hydrocarbons in which all carbon atoms are connected by single bonds

16.  Saturated – Each carbon atom is connected by single bonds

17. e.g. 2-methylheptane

18.  Naming of alkanes (p. 582) meth, eth, prop, ………. + ane e.g. methane e.g. methane

19.  Alkyl groups

20. Sources and uses of alkanes  Most from petroleum & natural gas  e.g. natural gas is 90 % methane  gasoline: heptane, isooctane, ….

21. Substitution reaction

22. Alkenes  Double bond between carbons  e.g. ethene  Naming: use alkane name, drop –ane, add –ene  Unsaturated (one or more double bond)

23.  Addition reaction:

24. Alkadienes  2 double bonds  e.g. 1,3 butadiene

25. Polymers  Lg. molecule made of repeating subunits  e.g. polyethylene

26. Alkynes  Triple bond  e.g. ethyne  Common name: acetylene

27. Cycloalkanes  e.g. cyclopentane

28. Aromatic hydrocarbons  e.g. benzene

29. Exhibit resonance:

30. para-dichlorobenzene para-dichlorobenzene

31. Examples of hydrocarbons 1.Petroleum  fractional distillation

33. 2.Rubber  vulcanization

34. Alcohols  Hydrocarbons with one or more hydroxyl (-OH) groups  e.g. 1-propanol  Drop the –e of propane and add -ol

35. Preparation of alcohols

36. Common alcohols  Methanol (wood alcohol)

37.  Ethanol (grain alcohol) often denatured = often denatured =

38.  Ethylene glycol

39. Halocarbons  Alkanes in which one or more halogens are substituted e.g. e.g. e.g. e.g. dichloromethane tetrachloromethane dichloromethane tetrachloromethane (carbon tetrachloride) (carbon tetrachloride)

40.  Dichloro-diphenyl-trichloroethane (DDT)

41.  Polytetrafluoroethylene (PTFE) or Teflon

42. Ethers  Two hydrocarbon groups are bonded to the same oxygen atom Dimethyl ether methyl ethyl ether

43. Aldehydes and Ketones  Substituted hydrocarbons with a carbonyl group

44. Aldehydes  The carbon of the carbonyl group is attached to at least one H

45. Aldehyde naming  Drop the –e from the alkane name anf add –al methanal ethanal methanal ethanal  ( common name formaldehyde)

46. Ketones  Both bonds of the carbonyl group attached to carbons

47. Ketone naming  Drop the –e of the alkane name and add –one propanone propanone (common name acetone) (common name acetone)

48. cinnamaldehyde

49. vanillin

50. piperine

51. Carboxylic Acids  Contain the carboxyl group

52. Carboxylic acid naming  Drop the –e and add –oic acid ethanoic acid ethanoic acid (common name: acetic acid) (common name: acetic acid)

53. Esters  General formula

54. Ester naming  Name of the R’ group first + name of acid represented before substitution of H with R’ group Drop –ic of acid name and add -ate Drop –ic of acid name and add -ate

55. Preparation of esters

56. saponification

57. Common esters

58. Interesting organic compounds 1.polystyrene

59. 2. trinitrotoluene