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1 2 3 4 5 6 7 8 Document related concepts no text concepts found Transcript 1. The Wurtz synthesis 8. Synthesis of alkenes from organic halides SET 2 R Hlg + 2 Na :B R CH CH2 R' R R + 2 NaHlg Hlg 2. The Clemmensen reduction R CH CH R' HHlg E 9. Synthesis of alkenes from alcohols R C R Zn(Hg)/cc HCl O CH2 H2O R R CH CH3 C O R CH3CH CH2 + HBr CH2 R CH3 CH3CHCH2 Cl + CH3CCH3 Cl 2 CH3 500 °C 300 °C 90 : 10 64 : 36 CH3 Br2 Cl : 99 Br 5. Nitration of ethane , p CH3CH2 NO2 + CH3 NO2 SR (CH2) n CH2 n= 1 Br2 n> 2 SR CH3 CH2 CH2 R CH CH2 R CH2CH3 + R' + Br Br2 n main product Br CH3CH2CH2 Br  Br Br Br Br  Br Br AE Br Br enantiomers a racemic mixture a bromonium ion 12. Hydration of alkenes R CH CH2 H AE R CH CH3 H2O R CH CH3 H O H R CH CH3 OH H 13. Hydrogenation of alkenes CH CH2 AR heterogeneous cat.: Pt, Pd, Raney Ni homogeneous cat.: metal complexes (Rh, Ru) H H 14. Epoxidation of cyclohexene with peroxycarboxylic acids BrCH2CH2CH2Br (CH2) CH3CHCH3 11. The reaction of cyclohexene with bromine room temp., 1 atm 7. The reaction of cycloalkanes with bromine CH2 AE catalyst+H2 6. Catalytic cracking of alkanes zeolite 500°C Br CH3 1 R' H Br a  complex CH3CHCH2 Br + CH3CCH3 R CH2CH2CH2CH2 R CH CH3 CH3 CH CH3 CH3 CH3 CH3 + dil. HNO3 E1 OH2 R 4. Halogenation of isobutane SR H2O 10. The reaction of propene with HBr 1. NH2NH2 2. KOH,  H2ON2 AN+E CH3CHCH3 R CH CH3 OH R 3. The Kishner–Wolff reduction R H CH2 CH Br + HBr O O H C O Ar O H O a peroxycarboxylic acid concerted C Ar AN ArCOOH O O cyclohexene oxide an epoxide or oxirane 1 15. The reaction of buta-1,3-diene with HBr 23. Aromatization of cyclopentadiene CH2 CH CH CH2 HBr CH2 CH CH CH2 Br Br H AE H CH3 CH CH CH2 CH2 CH CH CH2 Br H K H+ CH3 CH CH CH2 H Br H .. H H H cyclopentadienide anion K H 16. The Diels–Alder reaction H H C C 24. Selective oxidation of benzene and alkylbenzenes CHO CH2 CH + C  vagy h CH2 CH2 O O CH2R H a concerted reaction oxidation . 2 HC: >1200 °C 3 H2 methine radical HC CH + 2 Na H E+ Na C C + R'Hlg R NaHlg C C E + H+ H  complex 2 complex 26. The Friedel–Crafts alkylation R' R 20. Selective hydrogenation of acetylenes R' R Lindlar Pd/H2 C C R C C R' AR H H E + E = Cl, Br, NO2, SO2OH, R, RCO, D, CH2OH, ArN N SN CNa E E + 1 complex + H2 Na 19. The alkylation of acetylene C benzoic acid 25. Aromatic electrophilic substitution HC CH 18. Salt formation of acetylene R O maleic anhydride O 17. Synthesis of acetylene 2 CH4 COOH oxidation Na/liquid NH3 H R C H C RCHMe, RCHMe, + R' OH CH Me R CH Me Lewis acid Hlg or R CH CH2 + or H CH SE-Ar R Me 21. Hydration of acetylene H /H2SO4 HC CH + H2O AE Hg2+ O H2C CH OH CH3 C tautomeric rearrangement 27. The Friedel–Crafts acylation R H O + R 22. Hydration of substituted acetylenes Lewis acid (MLn) C Cl RC CH + H2O H /H2SO4 AE Hg2+ R CH CH2 OH SE-A R O C + Cl C  MLn O HCl MLn R C CH3 tautomeric O rearrangement 2 33. OH  Hlg exchange (mechanism) 28. Bromination of toluene CH2Br CH3 CH3 Br2, h Br2, FeBr3 SR SE-Ar SN1 CH3 Br OH + HHlg R + R Hlg O Hlg H HHlg: HCl, HBr HHlg terahydronaphthaline tetraline R Hlg H2O R COOH phthalic acid SN2 w = k [RHlg][:Nu ] R  Nu Hlg + :Nu inversion C  Hlg RC NO2 + Hlg :Nu +Hlg Nu : Hlg, HO, RO, HS, RS, CN, NO2 neutral nucleophiles: NH3, R'NH2, R'2NH R C SE-Ar Nu Hlg NO2 50°C Hlg 35. Mechanisms of nucleophilic substitutions RC HNO3, AcOH R XHlgn = PCl 3, PBr 3, PCl 5, PBr 5, SOCl 2 COOH 30. Nitration of naphthalene XHlgn OH SN Hlg = Cl, Br O naphthoquinone O Hlg 34. Synthesis of alkyl halides from alcohols 29. Partial hydrogenation and oxidation of naphthalene CrO3 R SN2 H2O Br Na/EtOH R H2O H main product SN1 racemization w = k [RHlg] 31. Sulfonation of naphthalene SO2OH 36. Mec1hanisms of eliminations 80 °C H2SO4 SE-Ar 140 °C H H  eliminations H 32. Partial hydrogenation and oxidation of anthracene O oxidation H H H .. R C C hydrogenation H +Hlg SO2OH HHlg :B R C C HHlg R Hlg  elimination E1 R C C Hlg 140 °C Hlg H E2 H Hlg .. R C C 9,10-dihydroanthracene R C C O 9,10-anthraquinone E1cB Hlg 3 37. Reduction of carbonyl compounds 44. Synthesis and transformations of ethylene oxide R R R CH2OH R'= H C O CH OH R' H R' R' LiAlH4 R COOR' HNu: HCl, ROH, NH3, RNH2, R2NH 39. Synthesis of alcohols from carboxylic acid derivatives with Grignard reagent R' O R C X 2. hydrolysis AN R X = Cl: acid chloride X = OR': ester R' R C OH R C O 1. R"MgHlg AN R=H R' = alkyl,aryl S CH2 OH CH OH OH R Hlg + NaNO2 R O CH H2O H + R' Hlg SN NaHlg O S O NO2 + R SN2 O SN1 N O ester of nitrous acid OH R CH R (CH2)2 O (CH2)2 R .. CH N O O OH , H H O N O R O CH N O 49. Reaction of aliphatic primary amines with nitrous acid 43. The Williamson ether synthesis R O Na (Ar) N 2 R CH CH2 R R O C H3C SN polar, aprotic solvent NaHlg .. N O ambident nucleophile 42. Inter- and intra-molecular dehydration of alcohols 2 R CH2CH2 OH R oxidation R' .. + 2. H+ S a sulfone H3C FriedelCrafts alkylation 2 H2O R 48. Nitro compound–nitronic acid rearrangement OH 1. oxidation R a sulfoxide .. :O .. R" electrophilic catalyst S 47. Synthesis of nitro compounds from organic halides 41. Synthesis of phenol E S a disulfide .. R C SE-Ar R R' R' H+ SH R' R, R' = alkyl, aryl + CH3CH=CH2 R oxidizing agents oxidation O R" R' mild conditions strong OH R R' 2. hydrolysis CH2CH2OH n 46. Oxidation of thioeters R' R' S O a sulfonic acid 40. Synthesis of alcohols from carbonyl compounds with Grignard reagent R, R' = H HO CH2CH2 O OH O R' R = alkyl,aryl O 45. Oxidation of thiols CH OH 1. 2 R'MgHlg poly(ethylene glycol), PEG n CH2 CH2 OH Nu SN H2O R CH2OH + R'OH R=H OH O catalytic hydrogenation (Pt/H2 or Raney Ni/H2) or hydride reduction (NaBH4 or LiAH4) 38. Reduction of esters CH2 CH2 HNu [O], Ag CH2 CH2 R O R' (Ar) R NH2 NaNO2, HCl 05°C N2 R OH + R O R + alkene 4 50. Reaction of aromatic primary amines with nitrous acid Ar O NaNO2, > 2 equiv HCl NH2 57. Acid- and base-catalyzed formation of enols Ar 05°C N N Cl .. RCH HO an aromatic diazonium chloride Ar C Ar N2 N Cu2Hlg2, HHlg N X Ar N2 an aromatic diazonium salt R' R' H Hlg = Cl, Br OH H N N Cl + X Y SE-Ar N N X X = activating substituent 53. The reaction of diazomethane with compounds having hydroxy function N2 CH3O Z R C CH3O-Z: aryl methyl ether, methyl ester, enol methyl ether AN R C O + H2O O R' OH C R' R' C OH unstable hydrate gem-diol H OH H C H H R R'OH R C H OR' H OR' R C OR' OH2 H O + R"MgHlg OR' CH3 OR' C O + H R' Al H R R' H Li C H OLi + AlH3 H3O R OMgHlg C H 3O Mg(OH)Hlg R" R' C OH R" C O + :CH2 R OH H2O H H C enolate anion H H CH3 C O O CH2 C H O H2O OH CH3 CH CH2 OH C H O E HC R' CH2 AN C O C carbanion O CH3 O :CH2 H AN R AN OH C H 56. Reduction of carbonyl compounds with complex metal hydrides H OH 61. Aldol reaction OR' H R' O R' C H CN 60. Reaction of carbonyl compounds with Grignard reagent (mechanism) O R C NR" HNR" H O 2 H R' R' C R' OR' C H H2O H2O, -OH  R CN C R' C C O + R' OH R R AN R R R E R C R' R' 55. Formation of acetals AN OH2 H3O HNR" 59. Cyanohydrin synthesis C O + CN R H2NR" R' R OH2 R C R" = H, alkyl, aryl, OH, NH2, NHPh 54. Reaction of carbonyl compounds with water R C R' OH O AN R' CH2N2 + HO Z RCH slow :OH2 C O + H2NR" C OH 58. Reaction of carbonyl compounds with nitrogen bases R HO-Z: HO Ar, HOOC R, HO CH H OH H3O R' H Y = deactivating substituent R C RCH fast C R' HO fast C RCH Hlg 52. Diazo coupling Y RCH O Cu2(CN)2, HCN N C slow 51. The Sandmeyer reactions O CH3 CH CH C H 5 62. Acid- and base-catalyzed -halogenation of carbonyl compounds C R H HO O R .. CH2 C CH2Br H R O Br2 C R Br O C R HBr OH R C CH3 a Br2 CH2 68. The Tollens test (a) and the Fehling test (b) C OH Br2 CH2Br R CBr3 O O R C CH3 CHIg3 R C HO O O R O + :CHIg3 C R + C OH O O CH2 CH C CH2 CH C R R CN ketoenol tautomerization CN C CH3 H + CH2O + Me2NH O R H2O C CH2 CH2 NMe 2 O R C O + H2NR' R AN+E H2O R C NR' R R' = H, alkyl, OH LiAlH4 or catalyst+H2 CH H3C C CH2 O C CH3 O 20 % H3C C O H 80 % H O OH .. R CN + (R N C: KHlg ambidens nukleofil SN2 R N C:) isonitrile SN1 sp2 CH R AN O  R sp3 Nu C X R AN R hydrolysis COOMgHlg Mg(OH)Hlg R COOH 72. Nucleophilic acyl substitutions X = Cl, OOCR', OR', OH, R sp2 NH2, NHR, NR2 C O :Nu = HO, R'O, R'COO; Nu neutral nucleophiles = H2O, NH3, 1° and 2° amines E O X X :Nu NHR' 73. Acid-catalyzed esterification/ester hydrolysis O 67. Keto–enol tautomerization of pentane-2,4-dione polar, aprotic solvent R MgHlg + CO2 + C reduction R C 71. Synthesis of carboxylic acids from carbon dioxide R 66. Reductive amination (reductive alkylation) R O R C .. :C N: :C N: 65. Mannich condensation R + Cu 2O red O precipitate CH2 CH2 C R conjugate addition C 70. Hlg  CN exchange O CH2 CH C AN R C H R Hlg + KCN OH HCN O Cu2+ reagents: CrO3/H2SO4 (Jones reagent), KMnO4, K2Cr2O7/H2SO4 HCHlg3 O 64. Reaction of HCN with ,-unsaturated carbonyl compounds O R silver mirror R CH2 OH HO O + 69. Oxidation of primary alcohols 63. The haloform reaction HIg2 Ag(NH3)2 + Ag C O C R b O CHBr R C OH H+ OH R C SN-Ac OH OH R'OH R C OH R C OH OH OR' H H+/+H+ OH R C OR' OH2 C CH3 O H2O OH R C OH R C OR' OR' H+ O R C OR' 6 74. Base-catalyzed hydrolysis of esters O O R C 80. Transformation of esters to other acid derivatives O R C OR' + :OH OR' SN-Ac R C O R C + R'O OH OH + R'OH O 75. Hydrolysis of carboxylic acid chlorides O + :OH2 R Cl SN-Ac R C Cl Cl R H OEt OH OEt CH3 C CH2 COOEt EtO O O H2O n = 1, 2 R NH2 C Hlg R' C O R COONa NaCl O R C O Cl + R COOH NH2 P2O5 R C H2O n = 1, 2 2 NH3 NH4Cl R C O R C NH2 H2O R C O O N H SN-Ac X O + HNR'2 R C NHR'2 O H2NR'2 X X: Cl, OOCR", OR" R': H, alkil, aril O R C NR'2 :HNR'2 SN-Ac X X R C O NR'2 85. Decarboxylation of 1,3-dicarbonyl compounds O O ( )n 84. Transformation of carboxylic acid derivatives to carboxamides 79. Direct synthesis of anhydrides O O Hlg = Cl, Br R'OH HCl R COOR' 2 R COOH O SN-Ac O SN-Ac 78. Transformation of acid chlorides to other acid derivatives O O  COOH O or AcCl R C C R C 83. Formation of lactams ( )n POCl3, PCl3, PBr3, PCl5, SOCl2 COOH R' NH3 O ( )n H COOH CH3 C CH2 COOEt 77. Synthesis of acid halides R + R' OH NH2 O R C R'OH SN-Ac ( )n + :CH2 COOEt OEt SN-Ac SN-Ac OH OH2 O O R C 82. Formation of lactones NaOEt CH3 C R COOR' v. base R COOR' + R COOH C 76. The Claisen ester condensation CH3 C SN-Ac H O O C OH2 R COOR" O NH3 81. Transformation of anhydrides to other acid derivatives O R C R" OH R C C COOH O  R C H C O H O C O CO2 R C C O R C C H R = OH - malonic acid R = Me - acetoacetic acid 7 86. Synthesis and structure of malonic ester sodium NaOEt CH2 :CH C O C O HC C O HC C O EtO EtO COOH EtO HC C O COOEt COOEt EtO EtO COOEt COOEt 90. Transamination C 6 C O O + NH2 CH R R' Na EtO HO: NaOEt CH2 COOEt COOEt EtOH COOEt RHlg :CH2 SN Na COOEt COOH H R CH R CH COOEt COOH COOH COOH H2O AN+E C COOH COOH N CH R HC N C R R' R' H2O COOH COOH HC NH2 + O R C R' tautomeric rearrangement 91. Synthesis of carboxylic acids from ethyl acetoacetate (the retro-Claisen reaction) 87. Synthesis of carboxylic acids using malonic ester synthesis COOEt COOH R OH R CH3CCHCOOEt  RCH2COOH CO2 CH3C O O CH COOEt CH3C .. + RCHCOOH CH3COO + RCH 2COO OH O H3O RCH2COOH 88. Synthesis and structure of the anion of ethyl acetoacetate CH3 C O CH2 C NaOEt O OEt CH3 C O :CH C CH3 CH3 CH3 C CH O C O C O CH C O O OEt OEt 92. Alcoholysis of phosgene OEt COCl2 C O HC 6 C O SN Me C CH COOEt R O dil. acid or base RO HCl SN-Ac RO C O RO dialkyl carbonate 93. Synthesis of carbamates (urethanes) R 1. NaOEt 2. RHlg HCl chlorocarbonic acid ester alkylchloroformate Na 89. Synthesis of ketones using acetoacetic ester synthesis Me C CH2 COOEt ROH C O SN-Ac O OEt Cl ROH C Me C CH COOH RO O CO2 SN-Ac Cl  AN R'HN O + R'NH2 C O R'N C O + ROH RO R = alkyl R' = H, alkyl, aryl Me C CH2R O 8 Related documents