Organic Chemistry 353-Chapter 6

Organic Chemistry 353-Chapter 6 - Propagation Steps...

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Writing Organic Reactions
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Types of Organic Reactions : Substitution
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Types of Organic Reactions : Elimination
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Types of Organic Reactions : Addition
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Bond Making and Bond Breaking Reaction Mechanism:
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Breaking Bonds
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Reactive Intermediates: Carbocation
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Reactive Intermediates: Free Radical
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Reactive Intermediates: Carbanion
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Reactive Intermediates: Carbene
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Bond Formation
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Bond Dissociation Energy
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Enthalpy of a Reaction
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Thermodynamics: Free Energy & Equilibrium
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Thermodynamics
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Thermodynamics: Enthalpy and Entropy Entropy
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18 Energy Diagrams For the general reaction: The energy diagram would be shown as:
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Two-Step Reaction
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Kinetics: Reaction Rates
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Chlorination of Methane Mechanism ? Thermodynamics ? Kinetics ? Clues ? From studying reactions…. .
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Chlorination of Methane Does not occur at RT in absence of light Best is a blue color High quantum yield
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Free-Radical Chain reaction Initiation Step
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Free-Radical Chain reaction
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Unformatted text preview: Propagation Steps Free-Radical Chain reaction Termination Reactions Reactivity with Other Halogens Reaction (kJ mol-1 ) F Cl Br I X 2 2 X +159 +243 +192 +151 X + H-R X-H + R-134 +4 +69 +138 R + X 2 R-X + X -293-106-100-84 H for reaction-427-102-31 +54 E act for Step 2 +5 +16 +78 +140 Reactivity order is fluorine > chlorine > bromine > iodine The order of reactivity is based on the values of E act for the first step of chain propagation and H for the entire chain propagation Selectivity Chlorination of Propane CH 3 CH 2 CH 3 + Cl 2 CH 2 CH 2 CH 3 CH 3 CH CH 3 + Cl Cl 1-chloropropane 40 % 2-chloropropane 60 % hv, 25 o C Stability of Free Radicals Selectivity (cont) Bromination of Propane CH 3 CH 2 CH 3 + Br 2 CH 2 CH 2 CH 3 CH 3 CH CH 3 + Br Br 1-bromopropane 3 % 2-bromopropane 97 % hv, 25 o C The Hammond Postulate...
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This note was uploaded on 02/02/2011 for the course CHEM 353 taught by Professor Walsh during the Spring '11 term at University of Evansville.

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Organic Chemistry 353-Chapter 6 - Propagation Steps...

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