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The document discusses several types of isomerism including structural isomers, stereoisomers, and optical isomers. It provides examples to illustrate structural isomers like positional and functional isomers. Stereoisomers include geometric isomers (cis-trans), optical isomers arising from chiral carbons, and diastereomers which are stereoisomers that are not mirror images. The document also discusses properties of meso compounds and uses Fischer projections to depict stereochemistry. Common organic reactions like substitution, addition, elimination, and oxidation are briefly overviewed with examples.
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- 1.
- 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
- 4. Structural isomer skeleton isomer positional isomer functional isomer Stereo isomer) (configuration)
- 5. Structural isomer skeleton isomer CH CH CH CH CH C H
- 6.
- 7. positional isomer C4H10O positional isomer
- 8. functional isomer CHO functional isomer O O CHO functional isomer 2 H C CH CH3 H3C C CH3 propanal propanone
- 9. 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
- 10. optical isomer (polarized light) (asymmetry) C chiral carbon C Br Br achiral carbon * C C Cl H H 3C H H 3C H 3C
- 11. Achiral molecule plane of polarized light optically inactive
- 12. Chiral molecule optically active
- 13. 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
- 14. Chirality Center Carbon hasfour different groups attached
- 15. CH CH Geometrica C=C H Cl Geometrical isomer C=C cis trans E E Z Sequenc priority
- 16. 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
- 17. Hi CH CH L C=C L H Cl Hi E- -chloro- -pentene E-iso Sequence rules C=C - priority Hi priority L priority Hi L Z priority Hi L E
- 18. L CH CH OH L C=C Hi CH CH Cl Hi Z E Hi CHZ- Z? CH OH Hi isomer C=C L H CH(CH L Z Z-isomer
- 19. COOH COOH HO H OH CH CH H -(-)-Lactic acid R R S? priority fischer projection Sequence rules , 2, 3 OH 1, 2 CH3 R S
- 20. Br Br NC H NC CH H CH R fischer projection priority , 2, 3 S R
- 21. 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
- 22. Fischer projection Fischerprojection
- 23. Diastereomers • stereoisomers mirror images • • • chiral centers • n chiral center n stereoisomers 23
- 24. 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 Diaster Diaster eomer 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
- 25. 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
- 26. C H3 C H3 Br C H Enanti H C Br H C Br omer Br C H C H3 C H3 A B Diaster Diaster eomer C H3 eomer H C Br H C Br C H3 C Moso compoun 26
- 27. 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
- 28. (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 H3 1S,2S)-(+)-Pseudophedrine Pseudophedrine (1R,2R)-(-)- 28
- 29. 1. substitution reaction ) OH + CH3CH2 Cl CH3CH2OH + Cl นิ 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
- 30. (Addition reaction) C C + A B C C A B CH2 CH2 + Cl2 CH2 CH2 Cl Cl CH3CH CH2 + Br2 CH3CH CH2 Br Br
- 31. Elimination reaction) X C C C C + X (HX) H Nu CH3CH2 Br + OH CH2 CH2 + H2O + Br (HBr)
- 32. H Lewis base C C C C + H2O OH H2SO4 CH3 CH2 OH CH2 CH2 + H2O ethanol ethene
- 33. Oxidation reaction) K2Cr2O7/H2 SO4 CH3 CH OH CH3 C O CH3 CH3 OH K2Cr2O7 O H + H
- 34. Reduction reaction) O H LiAlH4 CH3CH2 C OH CH3CH2 C OH H H2/ Pd CH3 CH2 CH CH2 CH3 CH2 CH2 CH3
- 35. 6. rearrangement reaction ) heat, catalyst CH3 CH2 CH2 CH3 CH3 CH CH3 CH3 heat, catalyst CH3 CH2 CH CH2 CH3 C CH2 CH3
- 36. Polymerization) Cl nCH2 CH Cl (CH2 CH) n vinyl chloride polyvinyl chloride nCH2 CH2 ( CH2 CH2 )n ethylene polyethylene