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Chapter 10 Solomons revised

Chapter 10 Solomons revised - Created by Professor William...

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Unformatted text preview: Created by Professor William Tam & Dr. Phillis Chang Ch. 10 - 1 Chapter 10 Radical Reactions About The Authors These Powerpoint Lecture Slides were created and prepared by Professor William Tam and his wife Dr. Phillis Chang. Professor William Tam received his B.Sc. at the University of Hong Kong in 1990 and his Ph.D. at the University of Toronto (Canada) in 1995. He was an NSERC postdoctoral fellow at the Imperial College (UK) and at Harvard University (USA). He joined the Department of Chemistry at the University of Guelph (Ontario, Canada) in 1998 and is currently a Full Professor and Associate Chair in the department. Professor Tam has received several awards in research and teaching, and according to Essential Science Indicators , he is currently ranked as the Top 1% most cited Chemists worldwide. He has published four books and over 80 scientific papers in top international journals such as J. Am. Chem. Soc., Angew. Chem., Org. Lett., and J. Org. Chem. Dr. Phillis Chang received her B.Sc. at New York University (USA) in 1994, her M.Sc. and Ph.D. in 1997 and 2001 at the University of Guelph (Canada). She lives in Guelph with her husband, William, and their son, Matthew. Ch. 10 - 2 Ch. 10 - 3 1. Introduction: How Radicals Form and How They React v Heterolysis A B ions heterolytic bond cleavage + A B v Homolysis A B radicals homolytic bond cleavage + A B Ch. 10 - 4 1A. Production of Radicals v Homolysis of covalent bonds ● Need heat or light (h ν ) R O O R heat R O 2 Cl Cl h ν Cl 2 (alkoxyl radical) (chlorine radical) Ch. 10 - 5 1B. Reactions of Radicals v Almost all small radicals are short-lived, highly reactive species Cl + H CH 3 Cl H + CH 3 R + C C C R C Ch. 10 - 6 2. Homolytic Bond Dissociation Energies (DH°) H + H H H Cl + Cl Cl Cl ∆ H o = - 436 kJ/mol ∆ H o = - 243 kJ/mol Bond formation is an exothermic process. H + H H H Cl + Cl Cl Cl ∆ H o = + 436 kJ/mol ∆ H o = + 243 kJ/mol Reactions in which only bond breaking occurs are always endothermic. Ch. 10 - 7 v The energies required to break covalent bonds homolytically are called homolytic bond dissociation energies , and they are usually abbreviated by the symbol DH ° Ch. 10 - 8 v Single-Bond Homolytic Dissociation Energies (DH°) at 25°C Bond Broken kJ/mol H – H 436 F – F 159 Cl – Cl 243 Br – Br 193 I – I 151 Ch. 10 - 9 v Single-Bond Homolytic Dissociation Energies (DH°) at 25°C Bond Broken kJ/mol H – F 570 H – Cl 432 H – Br 366 H – I 298 Ch. 10 - 10 v Single-Bond Homolytic Dissociation Energies (DH°) at 25°C Bond Broken kJ/mol Bond Broken kJ/mol H3C – H 440 H3C – F 461 H3C – Cl 352 H3C – Br 293 H3C – OH 387 H3C – I 240 H3C – OCH3 348 Ch. 10 - 11Ch....
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Chapter 10 Solomons revised - Created by Professor William...

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