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ไอโซเมอร์

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ไอโซเมอร์

  1. 1. AOIJAI WICHAISIRI
  2. 2.  isomerism isomer C2H6O CH3–CH2–OH O CH3–O–CH3 O C3H6O H3C C CH3 H3C CH2 C H ¤Õ âµ¹ áÍÅ äÎ´ì ´Õ
  3. 3. Structuralisomer skeletonisomerpositional isomer functionalisomer Stereo isomer) (configuration)
  4. 4. Structural isomer skeleton isomer  CH CH  CH CH  CH C H
  5. 5. C H
  6. 6. positional isomer C4H10O positional isomer
  7. 7. functional isomer CHO functional isomer O O CHO functional isomer 2 H C CH CH3 H3C C CH3 propanal propanone
  8. 8. Stereo isomer) geometrical isomer - (cis-trans isomer) H H3C CH 3 H3C H C C C C H H H CH 3 cis- 2-butene trans-2-butene
  9. 9. optical isomer (polarized light) (asymmetry) C chiral carbon C Br Br achiral carbon * C C Cl H H 3C H H 3C H 3C
  10. 10. Achiral molecule plane of polarized light optically inactive
  11. 11. Chiral molecule optically active
  12. 12. Achiral carbon• superimposible Chiral carbon• non- superimposible Br Br Br Br C C C C H H H H Cl H Cl H H3C CH3 H3C CH3 ËÁ 120Í§È ¹ Ø Ò
  13. 13. Chirality CenterCarbon has four different groups attached
  14. 14. CH CH Geometrica C=CH Cl Geometrical isomer C=C cis trans E E Z Sequenc priority
  15. 15. Sequence rules p Br > 17Cl > 8O > 7N > 6C > 1 multiple bond H H H H HH-C=O -C-O -C=C- -C-C- OC C C
  16. 16. Hi CH CH L C=C L H Cl Hi E- -chloro- -pentene E-iso Sequence rules C=C - priority Hi priority Lpriority Hi L Zpriority Hi L E
  17. 17. L CH CH OH L C=CHi CH CH Cl Hi ZE Hi CHZ- Z? CH OH Hi isomer C=C L H CH(CH L Z Z-isomer
  18. 18. COOH COOH HO H OH CH CH H-(-)-Lactic acid RR S? priority fischer projection Sequence rules , 2, 3 OH 1, 2 CH3 R S
  19. 19. Br Br NC HNC CH H CH R fischer projection priority , 2, 3 S R
  20. 20. CH=CH CH=CH H CH CH H CO H CH CH CO H S fischer projection priority fischer projection 3 , 2,2. priority , 2, 3 R ? S
  21. 21. Fischer projection Fischer projection
  22. 22. Diastereomers• stereoisomers mirror images••• chiral centers• n chiral center n stereoisomers 23
  23. 23. C H3 C H3 Enanti omer H C Br Br C H H C Br Br C H C 2H 5 C 2H 5 1 2 DiasterDiastereomer C H3 C H3 eomer Br C H H C Br H C Br Br C H C 2H 5 C 2H 5 Enanti 3 omer 4 24
  24. 24. Meso compounds • chiral centers stereoisomers • * * ,3-dibromobutane C H 3C HC HC H 3 stereoisomers Br Br C H3 C H3 C H3 C H3 Br C H H C Br H C Br Br C H H C Br Br C H H C Br Br C H C H3 C H3 C H3 C H3 A B C D 25
  25. 25. C H3 C H3Br C H Enanti H C Br H C Br omer Br C H C H3 C H3 A BDiaster Diastereomer C H3 eomer H C Br H C Br C H3 C Moso compoun 26
  26. 26. chiral cen• configuration chiral center (S) (R)• Stereoisomer A CH 3 ,3- Br (R) H dibromobutane C C-2 C-3 chiral centers3R)- ,3- (R) Br (2R, H C configurationdibromobutane (R) C H3 27
  27. 27. (R ) HO C H (S ) H C OH (S ) C H 3NH C H (R ) H C NHC H 3 C H3 C H3 (1R,2S)-(-)-Ephedrine (1S,2R)-(+)-Ephedrine (S ) (R ) H C OH HO C H (S ) (R ) C H 3NH C H H C NHC H 3 C H3 C H31S,2S)-(+)-Pseudophedrine Pseudophedrine (1R,2R)-(-)- 28
  28. 28. 1. substitution reaction ) OH + CH3CH2 Cl CH3CH2OH + Clนิ ลีอฟ วค โ ไ ล สรตั้ ต้ า งน สรผ ต ณ ์ อิ อ ที่ า ลิ ภั ฑ อ น หด อ ลุ อ ก H H2SO4 NO2 + HNO3 + H2O
  29. 29. (Addition reaction) C C + A B C C A B CH2 CH2 + Cl2 CH2 CH2 Cl ClCH3CH CH2 + Br2 CH3CH CH2 Br Br
  30. 30. Eliminationreaction) X C C C C + X (HX) H NuCH3CH2 Br + OH CH2 CH2 + H2O + Br (HBr)
  31. 31. H Lewis base C C C C + H2O OH H2SO4CH3 CH2 OH CH2 CH2 + H2O ethanol ethene
  32. 32. Oxidationreaction) K2Cr2O7/H2 SO4CH3 CH OH CH3 C O CH3 CH3 OH K2Cr2O7 O H + H
  33. 33. Reductionreaction) O H LiAlH4 CH3CH2 C OH CH3CH2 C OH H H2/ PdCH3 CH2 CH CH2 CH3 CH2 CH2 CH3
  34. 34. 6.rearrangement reaction ) heat, catalyst CH3 CH2 CH2 CH3 CH3 CH CH3 CH3 heat, catalyst CH3 CH2 CH CH2 CH3 C CH2 CH3
  35. 35. Polymerization) ClnCH2 CH Cl (CH2 CH) nvinyl chloride polyvinyl chloridenCH2 CH2 ( CH2 CH2 )nethylene polyethylene

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