H — C — C — OH

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