ORGANIC CHEMISTRY REACTIONS Functional Group Alkanes Reaction Reactants Conditions Products Cracking Long-chain Alkane Al2O3 & heat Alkane, Alkene CO2 + H2O Combustion Alkane, Oxygen Supply of O2 Alkane Hydrogenation Alkene, Hydrogen Heat, Ni catalyst Haloalkane, HCl Alkenes Halogenoalkanes Free-Radical Substitution Hydrogenation Alkane, Halogen UV light Alkene, Hydrogen Heat, Ni catalyst Alkane Elimination of Haloalkane NaOH, Haloalkane NaOH (ethanolic) NaOH (aq) [Alkene, H2O, NaX] [Alcohol, NaX] Dehydration of Alcohol Alcohol Al2O3 / conc. acid & heat Alkene + H2O Cracking Long-chain Alkane Al2O3 & heat Alkene Electrophilic Addition [H2] [H2O] [HBr] [Halogens] [Ni catalyst, heat] [H3PO4, heat] [Room Temp.] - Alkane Alcohol 1-Haloalkane Di-Haloalkane Oxidation [Alkene, H2O & O] [C bonded to 1 H] [C bonded to 0 H] Cold Dilute KMnO4 Diol Hot Conc. KMnO4 Aldehyde -> C.Acid Hot Conc. KMnO4 Ketone Addition Polymerisation Many Alkenes - Poly(alkene) Unsaturation Free-Radical Substitution Bromine, alkene Room temp. Orange - colourless Alkane, Halogen UV Light Haloalkane, HCl Electrophilic Addition Alkene, HX Alkene, X2 - 2nd- Haloalkane Di-Haloalkane Alcohol, HX Alcohol, PCl3 Ethanol, PCl5 Ethanol, SOCl2 KBr + H2SO4 Heat - Haloalkane, H2O Haloalkane, H3PO3 C2H5Cl, HCl, POCl3 C2H5Cl, HCl, SO2 Haloalkane, NaOH Haloalkane, KCN Haloalkane, NH3 Aqueous NaOH Ethanolic, Reflux NH3 Ethanolic, Heat Alcohol, NaX Nitrile, KX Alkylamine, HX Hydrolysis Haloalkane, H2O AgNO3, Reflux Alcohol, HBr Elimination Haloalkane, NaOH NaOH (ethanolic) Alkene, NaBr, H2O SN1 SN2 Tertiary Haloalkane Primary Haloalkane - Alcohol Alcohol Tests Haloalkane, AgNO3 & NH3 Dilute AgNO3 & Dilute NH3 AgCl – white, AgBr – cream, AgI - yellow Electrophilic Addition Alkene, Steam H3PO4, heat Alcohol Oxidation Alkene, H2O Cold dilute KMnO4 Diol Nucleophilic Substitution Haloalkane, NaOH Aqueous, heat Alcohol, NaX Aldehyde Ketone Carboxylic Acid LiAlH4 LiAlH4 LiAlH4 / H2 Ni Heat Primary Alcohol Secondary Alcohol Primary Alcohol Hydrolysis Ester, H2O, H2SO4 Ester, NaOH Dilute acid - Alcohol, C. Acid Alcohol Combustion Alcohol, O2 Heat CO2, H2O Substitution Alcohol, HX Alcohol, PCl3 Ethanol, PCl5 KBr + H2SO4 Heat - Haloalkane, H2O Haloalkane, H3PO3 C2H5Cl, HCl, POCl3 Substitution of Alcohols Nucleophilic Substitution Alcohols Reduction Carbonyl Compounds Carboxylic Acids Ethanol, SOCl2 - C2H5Cl, HCl, SO2 Na reaction Alcohol, Na - Na Alkoxide, H2 Oxidation Primary Alcohol Secondary Alcohol KMnO4 / K2Cr2O7 KMnO4 / K2Cr2O7 Aldehyde -> C.Acid Ketone Dehydration Alcohol Al2O3, Heat Alkene, H2O Esterification C.Acid, Alcohol H2SO4, Heat Reflux Ester + Water Synthesis Primary Alcohol Secondary Alcohol Heat, KMnO4 Heat, KMnO4 Aldehyde, H2O Ketone, H2O Reduction Aldehyde Ketone LiAlH4 LiAlH4 Primary Alcohol Secondary Alcohol Nucleophilic Addition Aldehyde, HCN Ketone, HCN KCN catalyst, heat KCN catalyst, heat Hydroxynitrile Hydroxynitrile 2,4-DNPH Test 2,4-DNPH, Carbonyl Compare ppt. with literature values Deep-Orange ppt Fehling’s Test Aldehyde, Cu2+ ions Alkaline solution, warm, no ketone Clear blue -> Red Tollens’ Test Aldehyde, AgNO3 Excess ammonia, warm, no ketone Ag+ -> Ag, Silver mirror Tri-iodomethane Aldehyde, I2, NaOH Alk solution of I2 Oxidation Primary Alcohol Aldehyde KMnO4 / K2Cr2O7 KMnO4 / K2Cr2O7 CHI3 (yellow ppt.), sodium salt Aldehyde -> C.Acid Carboxylic Acid Hydrolysis Nitrile, H2O Nitrile, H2O Ester, H2O Ester, NaOH HCl NaOH, Acidification H2SO4 catalyst Heat, Acidification C. Acid, NH4Cl Carboxylate, NH3 C. Acid, Alcohol Carboxylate, Alc. Redox Neutralisation Carbonates Metal, C. Acid C. Acid, Base C.Acid, Carbonate - Salt + Hydrogen Salt + Water Salt + CO2 + H2O Esterification C. Acid + Alcohol H2SO4 catalyst Ester + H2O Reduction C. Acid LiAlH4 Primary Alc, H2O Esterification C.Acid + Alcohol H2SO4 Ester + H2O Hydrolysis Ester + H2O Ester + NaOH H2SO4 Heat, Acidification C. Acid + Alcohol Carboxylate, Alc Nucleophilic Substitution Haloalkane + NH3 Ethanolic NH3, Heat, Pressure Amine + HBr Haloalkane + KCN Ethanolic KCN, Heat under Reflux Nitrile + HBr Carbonyl + HCN - Hydroxynitrile Nitrile + H2O Nitrile + H2O HCl NaOH, Acidification C. Acid + NH4Cl Carboxylate, NH3 Esters Nitrogen Compounds Hydrolysis