Download Organic Chemistry I Reactions Cheat Sheet and more Cheat Sheet Organic Chemistry in PDF only on Docsity! H. Kim for Chem 30B 1 Handout: Organic Chemistry Reactions Reactions Organized by Compound Families Alkanes 1. Combustion 2. Halogenation Alkenes and Alkynes 1. Additions: hydrogenation, halogenation, hydrohalogenation, hydration 2. Polymerization Aromatic Compounds Substitutions: nitration, halogenation, sulfonation Alcohols 1. Elimination: dehydration 2. Oxidations Thiols Oxidation Amines Acid-Base reactions Aldehydes and Ketones 1. Addition: Acetal/hemiacetal formation by alcohol addition (Reverse rxn: Acetal hydrolysis with acid) 2. Oxidation and Reduction for aldehydes (*Ketones go through reduction only) Carboxylic Acids 1. Substitutions: esterification, amidation (Reverse rxns: ester hydrolysis with acid or base, amide hydrolysis with acid or base) 2. Acid-base reactions Phosphoric acid and Phosphates Phosphoric acid: Esterification with alcohol Phosphates: Phosphorylation H. Kim for Chem 30B 2 Reactions Organized by Reaction Type Family Reaction Example 1. ADDITION Alkenes and alkynes Hydrogenation Halogenation Hydro- halogenation Markonikov’s Rule applies: H adds to C with more Hs already. Hydration Markonikov’s Rule applies. Aldehydes and ketones Addition of alcohol to get hemiacetals or acetals 2. SUBSTITUTION Aromatic compounds Nitration Halogenation Sulfonation Carboxylic acids Esterification with alcohol Amidation with amine Phosphoric acid and Phosphates Phosphoric acid: Esterification with alcohol Phosphates: Phosphorylation C C H H H H + H2 Pd catalyst C C H H H H H H C C HH C C H H H H H H + 2 H2 Pd catalyst C C H H H H + Cl2 (or Br2) C C H H H H Cl Cl H3C C O H(R) + CH3CH2OH H3C C OH H(R) O CH2CH3 hemiacetal H3C C O H(R) O CH2CH3 CH2CH3 acetal H+ catalyst + CH3CH2OH H+ catalyst + H2O + HNO3 H2SO4 catalyst NO2 + Cl2 (or Br2) ClFeCl3 (or FeBr3) catalyst + SO3 H2SO4 catalyst SO3H H3C C O OH + CH3CH2OH H+ catalyst H3C C O OCH2CH3 + H2O H3C C O OH + CH3NH2 heat H3C C O NHCH3 + H2O HO P O OH + CH3OH OH HO P O OCH3 OH + H2O O P O O + ROH O- RO P O O- O- + EnergyAdenosine P O P O- O O O- O- O P O O O- Adenosine P O- O O- + C C H CH3 H H + HCl (or HBr) C C H CH3 H H H Cl C C H CH3 H H + H2O C C H CH3 H H H OHH+ catalyst
