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BarCharts,Inc.® WORLD’S #1 ACADEMIC OUTLINE FEATURES OF AN ORGANIC REACTION Mechanism: Describes the overall reaction using a series of simple steps. Stoichiometry: Calculate reactant and product masses using the balanced equation and molar masses. Kinetics: The study of the reaction rate and mechanism. Theoretical yield: Mass of product given by a complete reaction; %yield=100%x(product mass)÷(theoretical yield). Equilibrium: Reaction does not proceed to completion, instead, it reaches a balanced state of forward and reverse reactions. Major reaction types: • Acid • Base • Oxidation Reduction • Condensation • Substitution (SN1, SN2) • Ionic Reaction • • • • • Elimination (E1, E2) Cyclization Hydrolysis Addition Radical reaction ORGANIC ACID AND BASE ALKENE Acid: Properties: Similar to alkane; non-polar, flammable • Electron-pair acceptor (Lewis acid) • Proton donor (Bronsted-Lowry acid); example: carboxylic acid • Electron-pair donor (Lewis base) • Proton acceptor (Bronsted-Lowry base); example: amine Factors enhancing acid strength (HA): • Weaker H-A bond • Greater electronegativity of “A” • Inductive effect of substituent on “A” (electron withdrawal enhances transfer). • More “s” character in hybrid orbital (s-orbital is lower in energy than p-orbital) • Resonance stabilized conjugate base (A-) Factors enhancing base strength: • Reverse of acid-strength guidelines A base is a nucleophile; Electronic effects which shift electron density to the atom with the lone-pair increases base-strength. • Diels Alder: form cyclic alkene • Friedel-Crafts: add acyl or akyl group • Grignard: add alkyl or aryl group • Wolf-Kirschner, Clemmenson: reduce ketone to alkane • Wittig: convert aldehyde/ketone to alkene KINETICS AND REACTION MECHANISM Energy T