Organic Chemistry Chemistry Notes PDF

O O O O O O O < < < < < < - O OH NR2...

O O O O O O O < < < < < < - O OH NR2 OR CH3 H Cl O H O H + + 1 N 2 - + R 1 N R 2 OH R R O H  – – – – – – O H C6H11 H O O + H2N-OH N C6H11 R N C6H11 R R + N C N O C N OH + O C OH H11C6 N C6H11 N C6H11 H H O O H R N C6H11 R O C N C6H11 N C6H11 O C N C6H11 H  O O 2 1 + HO R 1 R 2 + X H R X R O – – – 2 O O prim./sek. R 2 R 1 + Amin oder H N R 1 N + X H Carbonsäureamid R X NH3 R 3 3 R O OH OH Hydroxylamin H N R 1 N + X H Hydroxamsäure H H O NH2 NH2 Hydrazin H N R 1 N + X H Carbonsäurehydrazid H H  O O 1 R 2 + HO - 1 - + R 2 OH R O R O O O O O O O O < < < < < < - O OH NR2 OR CH3 H Cl O OH + H2O OH H H O Cl OH OH Cl OH OH Cl H O Chloralhydrat Ninhydrin  R O OH + ROH, - H2O (H+) O + HO R O O H H R + H2O, - ROH (H+) H R Halbacetal Acetal OH H O N CH3 H O H H CH3 O OH H HO OH Methylendioxymetamphetamin (MDMA, Ecstasy) H OH cyclisches Acetal Glucose (α-D-Glucopyranose) cyclisches Halbacetal  1 OH 1 1 1 O R R + H+, - H2O R R + H N N + + N N+ 2 2 + H2O, - H 2 2 H R H R H R H R Halbaminal Carbenium-Iminium-Ion O H + H+, - H2O H H - H+ H + H N + + N N+ + N H H + H2O, - H H H H H +H H Carbenium-Iminium-Ion Imin O R + H+, - H2O R R - H+ R + H N + + N N+ + N H H + H2O, - H H H H H +H H prim. Amin Carbenium-Iminium-Ion Azomethin OH - H2O (H+) OH O + H N + N H + H2O (H ) Hydroxylamin Oxim NH2 - H2O (H+) NH2 O + H N + N H + H2O (H ) Hydrazin Hydrazon O O H - H2O (H+) H N N O + H N NH2 N NH2 + H2O (H+) H Semicarbazid Semicarbazon  3 1 3 1 3 1 3 1 R CH2 R + H+, - H2O R CH2 R R CH2 R - H+ R CH R O + H N + + N N+ 4 N 2 R 4 R 2 + H2O, - H R 4 R 2 R 4 R 2 + H+ R R sek. Amin Carbenium-Iminium-Ion Enamin O O H - H2O (H+) NH2 O + H N O CH3 H + H2O (H+) O CH3 Acetessigester Enamin  1 R 3 1 3 1 3 1 2 R R + H+, - H2O R R R R + R1R2NH, - H+ 3 N R R O + H N + N N+ + 1 2 R 2 4 2 + H2O, - H+ 4 2 4 2 + H , -R R NH 4 N R R R R R R R 1 R sek. Amin Carbenium-Iminium-Ion Aminal CH3 CH3 N CH3 H3C N CH3 H2N Hexetidin  4 R 4 3 1 + 3 1 3 1 + O - H+ R R R + H , - H2O R R R R CH2 R 5 R 3 1 O R O + H N + N N+ 4 N H R 2 + H2O, - H+ H R 2 H R 2 R - O + H+ R 5 H R 2 5 CH2 R Amin Carbenium-Iminium-Ion Mannich-Base – H3C H H OH H3C NH + O + O N O H3C H - H2O H OH H3C – ² H3C H3C O O - NH N SO 3 H5C6 N + H2C O + NaHSO3 H5C6 N Na + + H2O N N CH3 CH3 H3C H3C Metamizol-Natrium – O O O O O O H2N H2N S S S S NH O NH2 + H2C O O + H2O Cl NH2 Cl N H Hydrochlorothiazid  HO HO R (H+) + R O OH HO + H+ HO R - H2O R + OH H CH3 N (H+) O CH3 + H+ N CH3 N CH3 N R R N - H2O N+ R HO CH3 CH3  HO R HO + HO +H R R - H2O - H+ + HO OH OH H3C CH3 H3C CH3 CH3 O O O O O + O (H+) HO OH Ox. HO OH OH 2 + R H - H2O R R  HO 3S O SO 3H H H H H OH HO HO 3S OH HO SO 3H - 2 H2O (H2SO4) HO 3S H H SO 3H HO 3S H SO 3H [O] O O+ HO 3S OH HO SO 3H HO 3S OH HO SO 3H + HO HO HO OH HO OH + +H HO O + + - 2 H2O OH OH  Br OH KBr OH Br OH + HO OH H2SO4 OH O HO Ox. HO + + Br OH O O OH OH O Br O O  N O O 3+ O O Fe N O O N – – – – – O OH OH O OH H3C O O OH OH Phenol Salicylsäure Acetylsalicylsäure Cyclohexanol geht geht besser GEHT NICHT! GEHT NICHT!  ³ OH OH N OH O OH O OH o-Hydroxybenzoesäure Brenzkatechin / Catechol Hydroxamsäure (Salicylsäure) ³ ³ ³  OH OH H COOH HO HO NH2 HO N CH3 H H2N ³ HO HO HO Noradrenalin Adrenalin Levodopa OH HO NH2 H COOH HO HO N CH3 CH3 H2N HO CH3 HO HO Dopamin Isoprenalin Methyldopa OH O OH O H CH3 N OH OH O H3C O Salicylsäure O H Bufexamac Vanillin  O O O H3C N N H OH N O HO H N H2N N OH O NH2 O HO N O O N O H NH HN O N N H H HO O NH N OH O N O + OH HO N N O O OH HO N H O  – – – O O – – O N+ O N+ H O 2N O O 1 – R C 2 N+ N+ C R + NO 2 – O – O O H 2 1 C R R C 2 C H R 1 R C 1 2 O O 3 4 O NO 2 + – N O H O – O OH- O O H H O O 2N + N + -H2O R O– H - COO - COO R  H 3C HO O O N CH3 H3C H 3C O H H H CH3 O OH H N H N CH3 CH3 O O Hydromorphon Oxycodon Methadon F N O X OH X = Cl: Haloperidol X = Br: Bromperidol O O CH3 CH3 CH3 H H 3C HO H3C O O O O OH H HO O HO O H OH Digitoxin  – – O – O O N+ O 2N O HNO3 (rauchend) H3 C CH3 / OH- R N+ R – R NO 2 -H2O H O H3C O –  CH3 O CH3 O N N CH3 O CH3 O H3C N H2N H Procain Tetracain N CH3 H3C OH H N N CH3 O O CH3 CH3 O Lidocain Atropin – O – O N+ O 2N O O H2SO4 / OH - R N+ NO 2 + NO 3 - NO 2 H3 C CH3 H O – - HSO4- -H2O - H2O H3C O  3 R NaNO2 / HCl R + N NH2 N N N 1 2 4 – NH2 N H OH · 2 HCl 2-Naphthol N-(1-Naphthyl)ethylendiamin- (β-Naphthol) dihydrochlorid (Bratton-Marshall-Reagenz)  H2O / h· COOH oder COOH O O O H2O (H+) / H 2N S NH O H2 N S NH2 O O HO H2O / h· Cl Cl oder Furosemid H2O (H+) / O H3C COOH H O N NH2 HO O H2O (H+) / O O 2N N O 2N NH2 Nitrazepam  - - N N + + - N N N SO 3 - N N SO 3 N R R - - N SO 3 + + - O N N SO 3 - O N