H2 Chemistry 9729 - Organic Chemistry reaction list SGExams ver

H2 CHEMISTRY 9729 Organic Chemistry Notes FEBRUARY 23, 2020 By Marcus Soh Victoria Junior College 2018-2019

Page | 2 Table of Contents ALKANES ................................................................................................................................................................................................. 4 ALKENES ................................................................................................................................................................................................. 5 HALOGENOALKANES ............................................................................................................................................................................... 8 ARENES ................................................................................................................................................................................................. 12 HALOGENOARENES ............................................................................................................................................................................... 16 HYDROXYLS (ALIPHATIC) ....................................................................................................................................................................... 18 HYDROXYLS (AROMATIC) ...................................................................................................................................................................... 22 CARBONYLS (ALDEHYDES) ..................................................................................................................................................................... 25 CARBONYLS (KETONES) ......................................................................................................................................................................... 28 CARBONYLS (CARBOXYLIC ACIDS) ......................................................................................................................................................... 30 CARBONYLS (ACYL CHLORIDES) ............................................................................................................................................................. 33 CARBONYLS (ESTERS) ............................................................................................................................................................................ 35 AMINES (ALIPHATIC) ............................................................................................................................................................................. 36 AMINES (AROMATIC) ............................................................................................................................................................................ 38 AMIDES ................................................................................................................................................................................................. 40 AMINO ACIDS ....................................................................................................................................................................................... 41 PROTEINS .............................................................................................................................................................................................. 42 DISTINGUISHING TESTS (by functional group) ....................................................................................................................................... 43 DISTINGUISHING TESTS (by reagent) .................................................................................................................................................... 45 REDUCING AGENTS ............................................................................................................................................................................... 47 OXIDISING AGENTS ............................................................................................................................................................................... 47 REACTION MECHANISMS ...................................................................................................................................................................... 48

Page | 3 Hydroxyls Carbonyls Alkanes Alkenes Halogeno- alkanes Alcohols Aldehydes Ketones Carboxylic acids Acyl chloride Ester C C C C R X R OH C OR H CR O R' C O OH R C O Cl R C O O R R' Free radical substitution Combustion Combustion Reduction Oxidation Electrophilic addition Elimination Nucleophilic substitution Acid-metal Nucleophilic substitution Condensation (elimination) Oxidation Nucleophilic addition Condensation Reduction Oxidation Iodoform test Nucleophilic addition Condensation Reduction Iodoform test Acid-metal Acid-base Condensation Conversion to acyl chloride Reduction De-carboxylation Hydrolysis Condensation Acid hydrolysis Alkaline hydrolysis Arenes Halogenoarenes Phenols Amines Phenylamines Amides Proteins X OH N R R' R'' NH2 R C N R' O H NH2 C H R C N C H R CO2H O H Addition Electrophilic substitution Hydrolysis Nucleophilic substitution Acid-metal Acid-base Nucleophilic substitution Electrophilic substitution Neutralisation Nucleophilic substitution Condensation Neutralisation Nucleophilic substitution Condensation Electrophilic substitution Acid hydrolysis Alkaline hydrolysis Reduction Acid-base catalysed hydrolysis Enzymatic hydrolysis Markonikov’s rule: For unsymmetrical alkenes, the electrophile will go to the carbon with the greater number of hydrogen bonded to it. This is to produce a more stable carbocation. Functional groups attached to benzylic carbons (the first carbon bonded directly to the benzene ring) can undergo the same reactions as if they were not bonded to a benzene ring. Phenol (-OH) and Phenylamine (-NH2) groups are very activating groups. Hence, reactions that used to need a catalyst do not need a catalyst anymore. Methanoic acid (HCOOH) and ethandioic acid (HO2C-CO2H) are unstable in the presence of acidified KMnO4 and will be oxidised to CO2 and H2O. Note: Always specify the medium and the reactants. Note: Nu refers to Nucleophile, E refers to Electrophile and X is a Halogen.

Previous: -- | Current: Alkanes | Next: Alkenes Page | 4 ALKANES Name of Reaction Starting compound Reagents and Conditions Products Reaction Mechanism / Chemical Equation Notes PREPARATION Reduction (alkene) C C H H H H ethene H2 gas, Ni catalyst, heat OR H2 gas, Pt or Pd catalyst, r.t.p. CH3CH3 C2H4 + H2 → C2H6 Produces alkanes C-C Addition (benzene) benzene H2, Ni, 150°C, high pressure cyclohexane C6H12 + 3H2 Produces cyclohexane REACTIONS Combustion C C H H HH H H ethane Limited O2, heat CO (g) + H2O (g) C2H6 + 5/2O2 → 2CO + 3H2O Excess O2, heat CO2 (g) + H2O (g) C2H6 + 7/2O2 → 2CO + 3H2O Free Radical Substitution C H H H H methane Limited Cl2 (g) or Br2 (g), UV light C H H Cl H chloroethane Produces halogenoalkanes R-X Excess Cl2 (g) or Br2 (g), UV light C Cl Cl Cl Cl tetrachloromethane CH4 + Cl2 → CH3Cl + HCl CH3Cl + Cl2 → CH2Cl2 + HCl CH2Cl2 + Cl2 → CHCl3 + HCl CHCl3 + Cl2 → CCl4 + HCl

Previous: Alkanes | Current: Alkenes | Next: Halogenoalkanes Page | 5 ALKENES Name of Reaction Starting compound Reagents and Conditions Products Reaction Mechanism / Chemical Equation Notes PREPARATION Elimination (halogeno- alkane) C C H Cl HH H H chloroethane NaOH in ethanol, heat C C H H H H ethane (major product) CH3CH2Cl → CH2=CH2 + HCl Produces alkenes Condensation or elimination (alcohol) C C H OH HH H H ethanol Excess conc. H2S