ORG CHEM REAGENTS/RXNS – Flashcards
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Methane to bromomethane
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FRS Bromine Uv light
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Ethene to 1,2-dibromoethene (Absence of uv)
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Electrophilic addition Bromine (liq) Rtp OR Bromine (aq) rtp Side product: 1-bromoethanol
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Ethene to 1-bromoethene (Absence of uv)
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Electrophilic addition HBr Rtp MARKONIKOV: ADD H to C with more H initially
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Benzene to nitrobenzene
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Electrophilic sub Conc NH3, conc H2SO4, 55 °C
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Benzene to chlorobenzene
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Electrophilic sub Cl, anhydrous FeCl3/AlCl3, warm
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Ethene to ethanol
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E addition Conc H2SO4, water, warm OR Conc H3PO4, 300°C, 60atm, steam
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Ethene to ethane
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E addition H2 (g) Ni/Pt/Pd High temp and pressure
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Ethene to 1-2diethanol
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Mild oxidation KMnO4, dil H2SO4/NaOH, cold (Form brown MnO2)
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Alkene to CO2/H2O OR aldehyde or ketone
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Oxidative cleavage KMnO4, dil H2SO4/NaOH Heat
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Ethylbenzene to benzoic acid
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Side chain oxidation KMnO4, dil H2S04, heat
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Methylbenzene to 2-chloromethylbenzene/2-nitromethylbenzene
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E sub SAME as benzene but less vigorous (30°C)
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Chlorobenzene (or other e withdrawing substituents) to chloro/nitromethylbenzene
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E sub Same but temp > 55°C
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Chloromethane to methanol
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Nu sub Naoh (aq), heat
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Chloromethane to amine
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Nu sub Ethanolic conc hno3, heat in sealed tube
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Chloromethane to nitrile
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Nu sub Ethanolic KCN Heat
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Nitrile to amine
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Reduction LiAlH4 in dry ether
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Nitrile to carb acid
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Acid hydrolysis Dil H2SO4, heat
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Nitrile to carbolxylate ion
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Alkali hydrolysis Dil NaOH, heat
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Chloroethane to ethene
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Elimination Ethanolic NaOH, heat
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Methanol to chloromethane
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1. PCl5, rt (forms POCl3 HCl) 2. PCl3, rt (forms H3PO3) 3. SOCl2, warm (forms SO2, HCl) 4. HCl, heat 5. NaBr, conc H2SO4, heat 6. (3° alcohol): ZnCl2, heat
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Alcohol to alkene
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Dehydration (elimination) Excess conc H2S04, 170°C OR Al2O3, heat
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Primary alcohol to carb acid
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Oxidation K2Cr2O7/KMnO4, dik H2SO4, heat
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Primary alcohol to aldehyde
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Oxidation K2Cr2O7, dil H2SO4, heat with immediate distillation
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Alcohol to ester
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Condesation Carb acid Conc H2SO4, heat OR Acyl chloride, rtp (use phenoxide for this)
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2° alcohol to ketone
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Oxidation KMNO4/K2Cr2O7, dil H2SO4, heat
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Carb acid to prinary alcohols
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Reduction LiAlH4 in dry ether
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Aldehyde to primary alcohols/ketone to secondary alcohol
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Reduction LiAlH4 in dry ether NaBH4 in methanol H2 with Ni
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Alcohol with methyl grp tri-iodomethane test
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4I2, 6OH-, 5I-, 5H2O CHI3 yellow ppt Carboxylate ion
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Ketone/aldehyde with methyl grp tri iodomethane
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3I2, 5OH-, 4I-, 4H2O CHI3 yellow ppt Carboxylate ion
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Alcohol to ethoxide
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Acid base Na (s) Rtp
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Phenol to phenoxide
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Acid base Na (s) or NaOH (aq) Rtp
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Phenol to ester
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Condensation ACYL CHLORIDES ONLY Not carb acid Use phenoxide
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Phenol to 2,4,6- tribromophenol
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E sub Br2 (aq)
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Phenol to 2-4dibromophenol
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E sub Br2 (liq) CCl4
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Phenol to nitrophenol
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E sub At rtp Conc hno3: tri sub Dil hno3: mono sub
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Phenol to violet complex
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Ligand exchange Neutral Fe3+ (aq) Rtp
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Ester to carb acid/carboxylate ion and alcohol
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Hydrolysis 1. Acid: carb acid H2SO4 (aq), dil h2SO4 2. Alkali: carboxylate Naoh (aq) dil h2So4
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Carb acid to acyl chloride
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Nu acyl sub 1. PCl5, rt (hcl, pocl3) 2. pcl3, rt (h3po3) 3. Socl2, warm (so2, hcl)
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Acyl chloride to amides
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Excess 1°/2°/3° amine
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Carbonyl compound to nitrile
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Nu add/condesation HCN (aq) Trace KCN Cold (10-20 degrees)
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Carbonyl to get orange ppt
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Condensation 2,4-dinitrophenylhydrazine Rtp
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Silver mirror test (aldehyde test)
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Oxidation Tollens reagent (Ag (NH3) 2)+, naoh, heat Form Ag, ammonia, water, carboxylate
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Aldehyde to carb acid
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Oxidation Kmno4/k2cr2o7, dil h2So4, heat (good test)
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Fehlings test (aliphatic aldehyde)
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Oxidatiob Cu2+, naoh, heat Forms carboxylate, cu2o (reddish brown ppt), water
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Nitrobenzene to phenylamine
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Reduction 1. Sn, excess HCl, heat 2. NaOH (aq)
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Amine to ammonium salt
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Acid base rxn Acid, rtp
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Phenyl amine to tribromophenylamine
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Aq bromine, rt (yellow orange solution decolourise, white ppt formed)
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Amides to carb acid/amine
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Hydrolysis Dilute Acid/base Heat
