Organic [ ]n REACTION PATHWAYS < > < < < < < < Br— C — C — Br H Br | H—C — C — H H OH | used in antifreeze and for making terylene H—C — C — H H Br | Organic REACTION PATHWAYS Elimination H—CC — H ETHYNE (sp, b =180°) 1,1,2,2 TETRABROMOETHANE Oxidising Agent Cr2O72- / MnO4- / H+ Oxidation MnO4- / H+ ETHANE-1,2-DIOL 1,2-DIBROMOETHANE Addition H2 / Ni ~ 200°C C — C O OH < HO > used as petrol additive Electrophilic Addition Br2 (unsat. Test) OXALIC ACID Electrophilic Addition H2 / Ni ~ 200°C H—C — C — H H | Substitution Br2 / U.V. H—C — C — H + HBr H | Br >C = C < H —CH2—CH2— [ ]n Benzoyl Peroxide Catalyst Catalytic Cracking H2 / Ni Chain Rxn. Temp / Pressure Addition Polymerisation (free radical) ETHENE (sp2, b =120°) POLYETHENE ETHANE (sp3, b =109.5°) BROMOETHANE Hydrolysis dilute H2SO4 Elimination Heat > 170°C xs conc. H2SO4 FURTHER SUBSTITUTION Electrophilic Addition Markovnikov’s Rule KBr + conc H2SO4  HBr xs alcohol conc. H2SO4 < 170°C H H | H | H | FURTHER SUBSTITUTION | H — C — C — O — C — C — H H—C — C — H H | Br H—C — C — OH H | Fermentation | H—C — C H | O OC2H < ETHYL ETHANOATE HBr, PCl5, PCl3 + Na (Act. of OH) Sugar Barley Potatoes H H—C — C — H H | NH2 AMINOETHANE (1° Amine) NH3 (SN1, SN2) ETHOXY ETHANE (diethyl ether) Reflux with dil. aq. Alkali (SN1, SN2) Hydrolysis: [OH-] + H2O BROMOETHANE ETHANOL (1° Alcohol) H—C — C — O-Na+ + ½ H2 H | Hydrolysis H+ / OH- KCN Polar Solvent SN1/SN2 ascend the homologous Series Oxidation (First Stage) Cr2O72- / H+ MnO4- / H+ Reduction LiAlH4 Esterification conc. H2SO4 Sodium Ethoxide H—C — C H | O O+Na- < Decend Hofmann Degradation H—C — C — CN H | PROPANONITRILE H—C — C H | O < Used as breathyliser test H—C — C H | O OH < HCl Further Oxidation Cr2O72- / H+ NaOH NH3 SODIUM ETHANOATE conc. HCl H—C — C H | O O-NH4+ < ETHANOAMIDE ETHANAL (acetaldehyde) ETHANOIC ACID P2O5 Reduction LiAlH4 (4[H]) Dilute Acid (HCl) Ca(OH)2 H—C — C — C H | O OH < H—C — C — C H | O NH2 < (CH3COO)2Ca PROPANOAMIDE (1°) H—C — C — C — N< H | 2,4-dinitrophenylhydrazine H—C — CN H | Dehydrate P2O5 Red-Orange ppte Ethanal-2-4-dinitro- -phenylhydrazine PROPANOIC ACID 2,4-dinitrophenyl- hydrazine ETHANONITRILE BY: ALI LAKHANI