Benzene

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Benzene

  1. 6. Filipino BBQ goodness: puto (rice muffins)                                                                                                                                                        
  2. 21. Some of the early researchers in organic chemistry became intrigued by fragrant oils that could be extracted from certain plants. The compounds responsible for the aromas, had similar chemical properties. As a result, they were grouped together and called AROMATICS COMPOUNDS.
  3. 22. As more and more aromatic compounds were isolated and studied, chemist gradually realized that aromatic contained six carbon atoms and had low hydrogen – to – carbon ratios (relative to other hydrocarbon). They also realized that the term aromatic was not always accurate. Because there are many fragrant compounds do not have aromatic properties.
  4. 27. Kekule was to say later that he must have dozed off at this point. In his dream the black balls of carbon turned into black imps with forked tails that began racing around the room and would soon be upsetting the apparatus of the laboratory. He was ready to run the rascals out. Then, almost suddenly, the confusion died away as each imp grabbed the tail of the one ahead of him, the six forming a whirling circle. One hand of each imp held a tail, the other a white handkerchief--and they waved to him as the group whirled by. He said that he came awake with a start, realizing that the imps were acting out the formula for benzene . As his hand grabbed the sketching pencil, the imps were back to black balls again and the handkerchiefs had changed to hydrogen atoms. How simple the arrangement turned out to be. “ The carbon atoms of benzene form a ring.&quot;
  5. 36. Modern benzene structure
  6. 37. Nomenclature
  7. 38. <ul><li>When a single hydrogen of the benzene ring is replaced, the compound can be named as a derivative of benzene . </li></ul>
  8. 39. ethylbenzene bromobenzene chlorobenzene nitrobenzene CH 2 CH 3 Br Cl NO 2
  9. 40. <ul><li>A number of benzene derivatives are known by common names that are also IUPAC – accepted and are used preferentially over other possibilities. </li></ul>
  10. 41. Toluene Phenol Aniline Benzoic Acid CH 3 OH NH 2 C — OH ║ O
  11. 42. O ║ C – CH 3 O ║ C O ║ C – H
  12. 43. <ul><li>Compounds formed by replacing a hydrogen of benzene with more complex hydrocarbon group can be named by designating the benzene ring as substituent . </li></ul><ul><li>We called them phenyl group. </li></ul><ul><li>benzyl </li></ul>
  13. 44. CH 3 CHCH ═ CH 2 3 – phenyl – 1 – butene CH 3 — C — C — C — CH 3 ا ا ا ا ا ا Br Br 3 HC 3 HC 2,2 – dibromo – 4,4 – dimethyl – 3,3 – diphenylpentane
  14. 45. CH2 OH Cl 2 – benzyl – 4 – chlorophenol
  15. 46. <ul><li>When two groups are attached to a benzene ring, three isomeric structures are possible. They can be designated by the prefixes ortho ( o ), meta ( m ), and para ( p ): </li></ul>
  16. 47. O - bromochlorobenzene m – nitrobenzoic acid p - chlorotoluene Cl Br CO 2 H NO 2 CH 3 Cl
  17. 48. 1,2 – dimethylbenzene O – xylene 1,3 - dimethylbenzene m – xylene 1,4 - dimethylbenzene p - xylene CH 3 CH 3 CH 3 CH 3 CH 3 CH 3
  18. 49. <ul><li>When two or more groups are attached to a benzene ring, their positions can be indicated by numbering the carbon atoms of the ring so as to obtain the lowest possible numbers for the attachment positions. </li></ul><ul><li>Group that comes first in alphabetical order is given the lower number. </li></ul>
  19. 50. 1 – bromo – 2 – chloro – 4 – iodobenzene 2,4,6 – trinitrophenol 3 – bromo – 5 - nitrotoluene Br Cl I O 2 N NO 2 OH NO 2 CH 3 NO 2 Br
  20. 51. 1,3,5 – trinitrobenzene 2,4,6 - trinitrotoluene TNT NO 2 NO 2 NO 2 CH 3 NO 2 2 ON NO 2
  21. 52. Preparation <ul><li>Major sources of aromatic compounds are petroleum and coal tar – (a sticky, dark – colored material derived from coal. </li></ul><ul><li>Natural sources </li></ul><ul><li>Can be synthesize synthetically </li></ul>
  22. 53. Physical Properties
  23. 54. Physical Properties <ul><li>Similar to those of ALKANES & ALKENES </li></ul><ul><li>Non – Polar </li></ul><ul><li>Insoluble in water (hydrophobic) </li></ul><ul><li>Flammable </li></ul><ul><li>Low density in water </li></ul>
  24. 55. Chemical Properties
  25. 56. Benzene Reactions <ul><li>Halogenation </li></ul><ul><li>Nitration </li></ul><ul><li>Sulfonation </li></ul><ul><li>Alkylation </li></ul>
  26. 57. Industrial Applications
  27. 58. Medicine
  28. 59. Medicine
  29. 60. Antiseptic
  30. 61. Consumer Products
  31. 62. Disinfectant
  32. 63. Synthetic Fiber
  33. 64. Plastic
  34. 65. Preservatives
  35. 66. Dyes
  36. 67. Fuel Additives
  37. 68. – fin –

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