เอกสารประกอบการเรียน เคมีอินทรีย์ 1

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  • 1. 40233 11 11.1 1. 2. 3. 2 1. (Organaic compound) - - - - - - 2. (Inorganic compound) () 11 40233

2. 2 11.1 1. 2.3. C H O , N , S , P , Cl , Br , I () 4. 5. 6. () 7. 8. 9. CO2 H2O 10. 11. 11 40233 3. 3 4 = 4 4 CCCC 1. 3 2. 7 C H C Cl 6 C O C = O 5 C N C = N C N 3. 11.1.1 2 1. 1 2. ( ) 11 40233 4. 41. (Extended Structural Formula) H H H H H O HC= CH HCCCCOH H H H HCHHCHHNHHHCHHCCH CCCHH HCHHHCHHHHHH CHH O HHC HCCCCHHHHCHHH2. (Partially Extended Structural Formula) H H HC=CH CH2 = CH2 H H H O O HCCCCOH CH3 - CH2 - CH2 C - OH H H H CH3 - CH2 -CH2 COOH H HCH CHHHCCCCH HH CHHH 11 HH C HCH3H 40233CCHCH3CH2CHCH3CH3 5. 5HH H HH CCHCCCH HH HH2C H2CH2 CCH2CH23. (Condensed Structural Formula) 3.1 C () 3.2 C C 3.3 3.4 C H CH3 - CH2 - CH2 - CH2 CH = CH2 CH3CH2CH2CH2CH=CH2 CH3(CH2)3CH=CH2 O (CH3)2CH CH2CONH2 CH3 CH - CH2 C NH2 CH3 CH3CHCH2CONH2 CH3 H2C H2COOCH2 CH2 4. (Line-angle Drawing Structural Formula) 4.1 4.2 2 8 11 40233 6. 64.3 CH2 = CH CH2 CH3CH3 CH3CCH3CH3 CH2CH3CH3CHCHCHCH3C C CH2CH3CHCH2CH3CH2CH3OCH2OH 2 3 CH4 109.5o 1 C2H4 120o 1 C2H2 180o 11.2 CH2CHCH2 11 CH2COOH 40233 7. 7 11.2 3 CH4H HC 3()~109.5oHHHC2H4H C~120oCH~120o H~120oC2H2HCCHH HHHCCCHC3H8HHHC6H6H~109.5oH CH180oCCC CH~120o HC H: 2550 11 40233 8. 8 1. , H H H H H HCCCC=CH H H HCH H 2. H H H H HCCOCCH H H H H 3. H HCH H H H H H H H C C C C C C C H H H H H H H HCH H 4. H H H H H H H H H HC CCCNCC C=CH H H H H H H(CH3)2CHCH2CH=CH21.5.H H HCH HCH H H O H H HC CCCCC CH H H H H H H 11 40233CH3 CH2O CH2 CH3 O(CH3)3C(CH2)4CH3CH3(CH2)3NH(CH2)2CH=CH2 N(CH3)2CH CH2CO CH2CH(CH3)2 O 9. 96. H H HCHHCH H H H H HC C CCC= CH H H H HCH HCH H7.H C C C C H H HH8.H H C C HHH O C C C H C C C C H HH C H , CH3 CH2C(CH3)2CH(CH3) CH2CH=CH2H C H H HC C C CCH(CH3)2O CH C HOH9. HHH3 CHH C C C C H HCC H10.CCCOOH OOO HOH CH2CH3H H H C HH H C C C C H C C H H OH H H 11 OHOH 40233 10. 102. 1.(CH3)3C(CH2)3 CH32.(CH3)4C3.CH3(CH2)2COCH2CH34.(CH3)3C CH2CC(CH2)2 CH35. COOCH2C(CH3)36.CH3CH2C(CH3)2 CH2CONH2 CH3 CH3-C-CH2-CH2-CH2-CH3 CH3 CH3 CH3 C CH3 CH3 O CH3-CH2-CH2-C-CH2-CH3 CH3 CH3-C-CH2-CC-CH2-CH2-CH3 CH3 CH2 CH2 O CH3 CH2 CH-C-O-CH2-C-CH3 CH3 CH3 O CH3-CH2-C-CH2-C-NH2 CH37.OH CH3CH=C(CH2CH3)CH(OH)CH2Br CH3 CH=C-CH-CH2Br CH2- CH3 8.OH COOH 11 HC HCH C C HC C 40233OH COOHOO O O NH2OHBrOH OH O 11. 11 9.10.OCH2CH3COOCH2CH3 H2 CO H2C CH CH 3 H2C CH2 H2 COO-CH2-CH3 HC C CH HC CH2 C H2 OO O ... ... 2528 11 40233 12. 1211.1.2 (Isomerism) 1. 2. 4 5 11.3 C4H10 ( C) CH3 -CH2-CH2-CH3 CH3 CH-CH3 CH3-138.3 -159.4 ( C) -0.5 -11.720C (g/cm3) 0.573 0.551 : 5 2549 11 11 40233 13. 13 11.1 1. 2. 3. 1. 1 1. 2. 5 3. 2 11 40233 14. 14 3 () H H H H H H C C C C C H H H H H H1H H H H H C C C C H H H H H C H H H H C H H H H C C C H H H H C H H23 1. 5 12 C5H12 2. 1 3 3. 1 11 40233 15. 15 2 1. 5 1 2. 3. 1 2 3 ()H H H H H H C C C C C H H H H12HH C HH CH CH C HH C HHH H H H H C C C C H H H C H H3 11 40233 16. 16 3 () H HCH4 HHCCH H C H H5H HCCHH H H H C C C H H C H H 1. 5 1 10 C5H10 2. 5 3. 5 H2CH2 CH2CCH2CH2H2 C H2CH 2CCCH3 CH3 11 CH3CH2H2C CH H2 CCH3CH H2C CHCH3CH3 HC H2C CH2 40233 17. 17 1. 5 12 3 3 2. 5 1 10 5 5 3. 1. 2. 3. 1 () ( ) 4. 5. 3 C 3 C 4 , 5 11 40233 18. 18 1. 1.1 1.2 1.3 2. - CnH2n+2O - CnH2nO2 - CnH2nO - CnH2n - CnH2n-2 2 structural isomer stereoisomer . structural isomer 1. skeleton isomer CH3-CH2-CH2-CH2-CH3 C5H12 CH3-CH-CH2-CH3 C5H12 CH3 CH3 CH3 C - CH3 C5H12 CH3 11 40233 19. 192. position isomer ( C ) C3H8O CH3-CH2-CH2-OH CH3-CH-CH3 C3H8O OH 3. functional isomer CH3-CH2-CH2-OH C3H8O CH3-CH2-O-CH3 C3H8O 4. metamer isomer position isomer CH3-CH2-O-CH2-CH3 C4H10O C4H10O CH3-O-CH2-CH2-CH3 . stereo isomer (conformation isomer) (geometrical isomer ) (optical isomer) (geometrical isomer ) cistrans isomer (C = C) CH3 CH3 C=C cis isomer cis 2 - butene H H H CH3 C=C trans isomer trans 2 - butene H CH3 cis- trans C C 11 40233 20. 20 ( C 360 1. 6 1.1 1 1.2 4 1.3 () 12 1.4 1.1 1.2 1.3 1.1 1.2 C6H14 1.3 1.1 1.2 C6H12 11 40233 21. 212. 6 1 2.1 3 2.2 10 13 3. , -CH3 1. CH3 -C C-C=C=CH2 CH3 2. CH3 -CH2-CH- CH2-CH3 , CH3 -CH2-CH-CH3 CH3 CH2-CH3 3.-CH2-,-CH2-CH34.,5. CH3 O CH3,CH3 CH2CH=C CH2 CH3 CH3 CH3 CH2 COOH6. 7. CH3 CH=CH(CH2)2C(CH3)3, ,(CH3)3C(CH2)2CH=CH CH3 11 40233 22. 22O8. CH3 CH2 CO(CH2)2 CH3 9. CH3(CH2)3CHO 10. CH3COOH CH311., , ,CH2CH3CH CH3 CH3(CH3 CH2)2CO HCOO CH3 CH2,CH2CHCH2CH3CH3CH2=CH12.CH3CH=CH CH313.CH3CH,CH3CH3CH3 CH2CH2 CH3,CH2CH2CH2CH3CH2CH214. CH3 CH2 CH = CH CH2 CH3,CH3(CH2)3CH = CH215. (CH3)3N,CH3NH CH2 CH3 11 40233 23. 2311.2 1. 2. 3. 4. 11.2 1. 2. 1. 4 4. 1 2. 4 5. 3 3. 1 6. 10 cm3 2 1. 5. NaHCO3 0.5 mol/dm3 2. 6. Ca(OH)2 3. 7. 4. 1. 10 10 11 40233 24. 242. 1 0.5 cm3 3. 0.5 mol/dm3 2 cm3 2 cm3 2 cm3 4. 1- 3 + + 11.1 : 2550 NaHCO3 11 40233 Ca(OH)2 25. 25 1. 2. - 3. 4. NaHCO3 NaHCO3 CO2 Ca(OH)2 5. OH COOH 1. 2. 2 CH3CH2OH + 2Na 2 CH3 CH2ONa + H2 2 CH3COOH + 2Na 2 CH3COONa + H2 3. CH3COONa + H2O + CO2 CH3COOH + NaHCO3 4. (-OH) (-COOH) 11 40233 26. 265. 11.4 C=C CC C C CnH2n+2CnH2nCnH2n-2R-OHAr-OH R-O-R/-OH-O- O C OH O R C OO C HO- NH2 O C CRNH2O R C OH O R C O R/O 11 CHCH CH3-CH2-OH () () CH3-O-CH3 () OR C R/R-NH2 O CO CH3 C OHCH3CNH2 40233OCH3OOROHCH3 C HR C H CH4 CH2=CH2O CH3 C CH3 CH3-NH2 O H C NH2 27. 27 (Hydrocarbon) aliphatic alicyclic aromatic hydrocarbon hydrocarbon hydrocarbon O N O , N 1. CH3CH=C(CH3)2CH3CH2CHNH2 CH3CH3 OCOOH CH3CH3CH2COCH3 11 40233 28. 28CH3CH2CH2CH(CH2)2CH3 OH O CH3 -CH2-C-O-CH3CH3 CH2CONH2O OH 11 40233 29. 2911.3 1. 2. 4. 5. 6. 7. 8. 9. 3 1. (Aliphatic Hydrocarbon) (open chain) (straight chain) (branch chain) 3 (alkane) (alkene) (alkyne) 2. (Alicyclic Hydrocarbon) 3 (cycloalkane) (cycloalkene) (cycloalkyne) 3. (Aromatic Hydrocarbon) 11 40233 30. 30 - 2 1. (Saturated Hydrocarbon) 2. (Unsaturated Hydrocarbon) 1 11.3.1 1. 2. 3. 4. 5. 6. CO2 H2O 7. (substitution reaction) (addition reaction) 1. CO2 H2O 2. CO 2 H 2 O CO C 11 40233 31. 31 1. > 11 40233 36. 364. 1 . C3H8 C3H6 C3H6 C6H5- CH3 . C6H5- CH3 C6H14 . C4H10 C5H10 C5H10 . C6H6 C6H10 C6H6 5. A B C D A B C D . B D . B 11 40233 37. 3711.3.2 11.3.2.1 (Alkane and Cycloalkane) CnH2n+2 (CH4) ~109.5o 11.3 : 2550 IUPAC (International Union of Pure and Applied Chemistry) (Straight Chain) - (-ane) 1 = meth - 6 = hex - 2 = eth - 7 = hept - 3 = prop 8 = oct - 4 = but 9 = non - 5 = pent - 10 = dec - (branched chain) (alkyl group) 1 -R CnH2n+1 - yl 11 40233 38. 38 11.5 CH3CH3-CH2CH3-CH2-CH2CH3-CHCH3 CH3- CH2- CH2- CH2CH3-CH-CH2CH3 CH3-CH2-CHCH3 CH3 CH3-CCH3 CH3-CH2-CH2-CH2-CH2CH3-CH-CH2-CH2CH3 CH3 CH3-C-CH2CH3 CH3 CH3-CH2-CCH3 IUPAC methyl ethyl propyl 1-methylethyl methyl ethyl n-propyl iso-propylbutyl 2-methylpropyln-butyl iso-butyl1-methylpropylsec-butyl1,1-dimethylethyltert-butylpentyl 3-methylbutyln-pentyl iso-pentyl2,2-dimethylpropylneo-pentyl1,1-dimethylpropyltert-pentyl (branched chain) 1. 2. (alkyl group) 11 40233 39. 393. 4. 2 , 5. Alicyclic hydrocarbon 3 (cyclo-) 11.6 CH3- CH2- CH2- CH2- CH3 pentane CH3 12CH3CH23 C CH2 4 CH3CH2CH2 5C6CH2CH33 CH CH3CH3 654 CH33,3-dimethylhexane 3,3-CH3CH3CH 24-ethyl-2,3,4-trimethylhexane 4--2,3,4-CH3 1cyclobutane Methylcyclopentane CH3 11 40233 40. 40 1,2-dimethylcyclopentane 1,2-5 14 3CH32 CH3 n - , iso - , neo - CH4 methane propane CH3- CH2 -CH3 CH3- CH2- CH2- CH2- CH3 n - pentane CH3- CH - CH2- CH3 iso - pentane CH3 CH3 neo - pentane CH3- C - CH3 CH3 () 1. 2. 3. ( ) 4. 5. 3 C 1 4 C 5 17 C 18 11 40233 41. 416. 1.00 g/cm3 1. (combustion oxidation) O2 CXHY +Y x+ 4 +O2xCO2 +6O2Y H2O 24CO2 + 4H2O2. (substitution reaction) H Cl2 , Br2 halogination 2 (alkylhalide) (hydrogenhalide) CnH2n+2 + X2 light CnH2n+1X + HX HHCCCHHHHBrBrlightHH +HHBrCCCHHHHH +HBr3. (cracking or pyrolysis) 400 600 C CH3- CH2- CH2- CH3C4H8 + C3H6 + C2H6 + C2H4 + CH4 + H24. KMnO4 11 40233 42. 42 1. 2. 2.1 (catalytic reduction of alkene) H2 Ni Pt ( hydrogenation) Ni Pt CH2=CH2 + H2 / CH3- CH3 2.2 CH3- CH3 + Zn2+ + ClCH3- CH2- Cl + Zn + H+ 2.3 alkylhalide Na Wurtz reaction 2 CH3- CH2- Br + 2 Na CH3- CH2- CH2- CH3 + 2 NaBr 2.4 (Al2C3) HCl Al2C3 + 12H2O 4Al(OH)3 + 3CH4 Al2C3 + 12HCl 4AlCl3 + 3CH4 1. 2. 3. 1. 2. 1. 2. 3. KMnO4 KMnO4 11 40233 43. 43 1. 1 2 3 4 5 6 7 8 CH4 C2H6 C3H8 C4H10 C5H12 C6H14 C7H16 C8H18 ( C) -182.0 -183.3 -189.7 -138.4 -130.0 -95.0 -90.6 -56.8 ( C) -164.0 -88.6 -42.1 -0.5 36.1 69.0 98.4 125.7. . . 150 100 50 0 -5012345678 ( )-100 -150 -200 11 40233 44. 44. 15 C . 2. C 8 11 16 19 C8H18 C11H24 C16H34 C19H40 C8H16 C11H22 C16H32 C19H38 C8H17 C11H23 C16H33 C19H393. 1.2.3.4. CH3 - CH2 - CH2 CH CH - CH3 CH3 CH3 CH3 CH CH C - CH3 CH2 CH2 CH3 CH3 CH3 CH3- (CH2)4- CH - CH3 CH32,3-dimethylhexane3-ethyl-2,2-dimethylhexane2-methylheptaneCH3- CH2- CH2- CH - CH3 CH2- CH3 11 3-methylhexane 40233 45. 455.6.7. 8.9. 10. 11. CH3 CH3- C - CH2- CH3 CH3 CH3 CH2 CH3 CH2- C CH - CH3 CH3 CH2- CH3 CH3- (CH2)2- CH (CH2)4- CH3 CH3 CH3- CH2- CH CH - CH2- CH3 CH3 CH2- CH2- CH3 CH3 2,2-dimethylbutane3,4,4-trimethylheptane4-methylnonane 4-ethyl-3-methylheptane 1-ethyl-2-methylcyclohexaneCH2CH3CH3methylcyclopentaneCH3 CH3-CH-CH-CH2-CH3 CH2CH33-ethyl-2-methylpentane12. 2,3,4-trimethyloctane 13. cyclooctane 14. 3-ethyl-2,2-dimethylheptane 11 40233 46. 464. 1. 2,3-dimethylhexane 2. 3-ethyl-2,3- dimethylhexane3. 3-methylheptane 4. 4,4-diethyl-2,5,5trimethyloctane5. 2,3,4-trimethylpentane6. 3-ethyl-4,5-dimethyloctane7. ethylcyclopropane (CH3)2CHCHCH2CH2CH3 CH3 CH3 (CH3)2CHCCH2 CH2 CH3 CH2CH3 CH3 CH2CH(CH2)3CH3 CH3CH2CH3 (CH3)2CHCH2CC(CH3)2(CH2)2CH3 CH2 CH3 (CH3)2CHCHCH(CH3)2 CH3 CH3 CH3CH2CHCHCH(CH2)2CH3 H3CH2C CH3 CH2CH38. 9. 3- 10. 4--2,2- 11 CH3 CH2CH(CH2)2CH3 CH2CH3 CH2CH3 (CH3)3CCH2CH(CH2)3CH3 40233 47. 47 11. 1,3-H3CCH3CH2CH2CH3 (CH3)3CCH2CHCH(CH2)3CH3 CH312. 2,2,5--4- 5. 5.1 CH4 + 2O2 CO2 + 2H2O 5.2 3CO2 + 3H2O C3H6 + 4.5O2 5.3 C4H10 + 6.5O2 4CO2 + 5H2O 5.4 8CO2 + 9H2O C8H18 + 12.5O2 6. 6.1 CH3-CH2-CH2-CH2-CH2Cl + HCl CH3-CH2-CH2-CH2-CH3 + Cl2 3 CH2Cl-CH2-CH2-CH2-CH3 CH3-CHCl-CH2-CH2-CH3 6.2 + Cl2 1 ClCH3-CH2-CHCl-CH2-CH3+ HClCl 11 40233 48. 486.3 2- CH3-CH-CH3 + Cl2 CH3CH3-CH-CH2Cl + HCl CH3 2 CH3-CCl-CH3 CH3-CH-CH2Cl CH3 CH3 1. 2. 3. 8 4. 5. 6. 7. 11 40233 49. 4911.3.2.2 (Alkene and Cycloalkene) 1 CnH2n CnH2n-2 C H 2 C:H olefin n = 2 C2H4 H ~120o H ~120o C C o H ~120 H 11.4 : 2550 1. 3 (C 2 4 ) (C 5-18 ) 2. 3. 4. 5. 6. C 7. 11 40233 50. 50 IUPAC 1. C -ene 2. C 4 3. 2 -adiene 3 -atriene 1. C 2. 3. 4. 5. 1. cyclo 2. 11.7 CH2=CH2 CH2=CH-CH2-CH3 6 CH31 CH35 CH24 CH22 CHCH24 CH3 CH H3 CCH33 CH2 CH1 CH3CH35 CH 6 CH24 CH34,5-dimethyl-2-heptene 4,5--2-7 CH3CH3 3 CH IUPAC Ethene 1-butene 1- 2-hexene 2- 2 C2-ethyl-3-methyl-1-butene 2--3--1-1 CH2 11 40233 51. 51 CH3 1 CH22 CH4 C3 C5 CH3 IUPAC 3,4-dimethyl-1,3-pentadiene 3,4--1,3-CH3CyclopropeneCycloheptene 5 41 31 62 5CH32CH3 3 41-methyl-1-cyclopentene 1--1- 4-ethyl-3-methyl-1-cyclohexene 4--3--1-CH2CH3 2 3 ethylene CH2=CH2 CH3-CH=CH2 propylene CH3-CH2-CH=CH2 butylene CH3-C =CH2 iso-butylene CH3 CH2=C CH=CH2 isoprene CH3 3 (cis-) 11 40233 52. 52 (tran-) - - BB CABCA CACAB C=C 11.8 2-butene 2-butene -2- cis-2-butene -2- trans-2-butene 3 () HH CH CCH3CCH3CH3CCH3 H (C) (C) 11 -138.9 3.7 40233-105.5 0.8 53. 53 1. (addition reaction) 1.1 addition of hydrogen H2 hydrogenation Ni , Pt Pd Ni,Pt C+CCH2CH H Ni,Pt +H21.2 addition of halogens Cl 2 Br2 C+CCX2CX X X +X2 X1.3 addition of hydrogen halide HX HCl , HBr , HI CC+HXCCH X+HX X1.4 addition of water with acid H2SO4 (hydration) CC+H2OH+CCH OH + 11 H2OH+ 40233OH 54. 541.5 hydroxylation glycol formation KMnO4 MnO2 3CC+2KMnO4+4H2O3CC+2MnO2+ 2KOHOH OH2. 3. (polymerisation reaction) 200-250oC n(CH2=CH2)( CH2 CH2)n>1500 atm,catalyst 1. Br2/CCl4 Br2/CCl4 2. KMnO4 KMnO4 3. - - - 11 40233 55. 5511.3.2.3 (alkyne) C C CnH2n-2 C:H (C2H2) 180o 180oHCCH 11.5 : 2550 (C7H10) 1. IUPAC -yne CH3CH3 3 2 1 CH2 C C CH 4 CH2 5CH26 CH33-ethyl-3-methyl-1-hexyneCH2 CH3 2 1 3 CH3 CH C CH34 5 6 C CH CH CH3 7 8 CH2 CH35-ethyl-2,6-dimethyl -3-heptyne2. -C C- CHCH acetylene methylacetylene CHC-CH3 ethylacetylene CHC-CH2-CH3 CH3-CC-CH3 dimethylacetylene methylisopropylacetylene CH3-CC-CH-CH3 CH3 11 40233 56. 56 1. 2. 3. 4. 5. 11.9 2 3 4 5 6 7 8ethyne propyne 1-butyne 1-pentyne 1-hexyne 1-hepthyne 1-octyne C2H2 CHCH3 C3H4 CHC-CH3 C4H6 CHC-CH2-CH3 C5H8 CHC-CH2-CH2-CH3 C6H10 CHC(CH2)3 CH3 C7H12 CHC(CH2)4CH3 C8H14 CHC(CH2)5CH3 (C) (C)-80.8* -102.7 -125.7 -105.7 -131.9 -81.0 -79.3-84.0** -23.2 8.0 40.2 71.3 99.7 125.26. C > > 1. O2 3CO2 + 2H2O C3H4 + 4O2 11 40233 57. 572. 2.1 (hydrogenation) Ni , Pt Pd H2 Ni,Pt+ H2CCCHCHH +CCNi,Pt2H2CHCHH2.2 (halogenation) (X2) Cl2 Br2 HX X X2CCCX BrCCH+2Br2HCCC XBrBrHXXCXCX2BrH2.3 (HX) Br +CC2HBrCBrCHHHHCCCH +H2HBrHBrHCCCHHBrHH3. 1 3RCOOH + 3 CO2 + 8 MnO2 + 8KOH 3RC CH + 8KMnO4 + 4 H2O 2 O O 3RC - CR + 4 MnO2 + 4KOH 3RCCR + 4 KMn...

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