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chapter6 - Organic Chemistry William H Brown Christopher S...

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6- 6-1 Organic Organic Chemistry Chemistry William H. Brown William H. Brown Christopher S. Foote Christopher S. Foote Brent L. Iverson Brent L. Iverson
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6- 6-2 Reactions of Alkenes Chapter 6 Chapter 6
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6- 6-3 Characteristic Reactions Characteristic Reactions C C C C C C Br 2 ( HX) HCl H 2 O ( X 2 ) C C Br 2 ( X 2 ) H 2 O (X) C C H OH C C Br Br (X) C C HO Br (X) C C H Cl (X) Descriptive Name(s ) Re ac t io n + + + Bromination (halogenation) Hydrochlorination (hydrohalogenation) Hydration + Bromo(halo)hydrin formation
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6- 6-4 Characteristic Reactions Characteristic Reactions C C C C C C BH 3 OsO 4 H 2 C C Hg(OAc) 2 H 2 O C C BH 2 H C C HO OH C C H H C C HO HgOAc + + + Hydroboration Diol formation (oxidation) Hydrogenation (reduction) + Oxymercuration
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6- 6-5 Reaction Mechanisms Reaction Mechanisms A reaction mechanism describes how a reaction occurs which bonds are broken and which new ones are formed the order and relative rates of the various bond- breaking and bond-forming steps if in solution, the role of the solvent if there is a catalyst, the role of a catalyst the position of all atoms and energy of the entire system during the reaction
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6- 6-6 Gibbs Free Energy Gibbs Free Energy Gibbs free energy change, Gibbs free energy change, G G : : a thermodynamic G 0  = DH 0   TDS 0
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6- 6-7 Gibbs Free Energy Gibbs Free Energy a change in Gibbs free energy is directly related to chemical equilibrium summary of the relationships between G 0 , H 0 , S 0 , and the position of chemical equilibrium G 0  = -RT ln  K eq At higher temperatures when T Σ 0 Η 0 ανδ Γ 0 < 0, τηε ποσιτιον οφ εθυιλιβριυμ φαωορσ προδυχτσ Γ 0 0; τηε ποσιτιον οφεθυιλιβριυμ φαωορσρεαχταντσ Γ 0 < 0; τηε ποσιτιον οφεθυιλιβριυμ φαωορσπροδυχτσ Ατλοϖερτεμ περατυρεσ ϖηενΤ∆ Σ 0 < ∆ Η 0 ανδ Γ 0 < 0, τηε ποσιτιον οφ εθυιλιβριυμ φαωορσ προδυχτσ Η 0 0 Η 0 < 0 Σ 0 < 0 Σ 0 0
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6- 6-8 Energy Diagrams Energy Diagrams Enthalpy change, Enthalpy change, ∆ Η ∆ Η : : the difference in total
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6- 6-9 Energy Diagrams Energy Diagrams Energy diagram: Energy diagram: a graph showing the changes in energy that occur during a chemical reaction Reaction coordinate: Reaction coordinate: a measure in the change in positions of atoms during a reaction Reaction coordinate
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6- 10 Activation Energy Activation Energy Transition state: Transition state: an unstable species of maximum energy formed during the course of a reaction a maximum on an energy diagram Activation Energy, Activation Energy, G G : : the difference in Gibbs
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6- 11 Energy Diagram Energy Diagram a one-step reaction with no intermediate
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6- 12 Energy Diagram Energy Diagram A two-step reaction with one intermediate
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6- 13 Developing a Reaction Mechanism Developing a Reaction Mechanism How it is done design experiments to reveal details of a particular chemical
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