ch03 - Chapter 3 An Introduction to Organic Reactions and...

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Created by Professor William Tam & Dr. Phillis Chang Ch. 3 - 1 Chapter 3 An Introduction to Organic Reactions and Their Mechanisms Acids and Bases
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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. 2 - 2
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Ch. 3 - 3 1. Reactions and Their Mechanisms v Almost all organic reactions fall into one of four categories: Substitutions Additions Eliminations Rearrangements
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Ch. 3 - 4 Substitutions t Characteristic reactions of saturated compounds such as alkanes and alkyl halides and of aromatic compounds (even though they are unsaturated) t In a substitution, one group replaces another
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Ch. 3 - 5 v Examples H 3 C Br Na OMe MeOH H 3 C OMe Na Br + + Br Br + + H Br H Br h ν + CH 3 Cl AlCl 3 + H Cl H CH 3
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Ch. 3 - 6 Additions t Characteristic of compounds with multiple bonds t In an addition all parts of the adding reagent appear in the product; two molecules become one
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Ch. 3 - 7 v Examples Br Br + C C H H H H CCl 4 C C Br H H H H Br Cl Cl + HC CH CCl 4 C C Cl H Cl Cl H Cl 2
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Ch. 3 - 8 Eliminations t In an elimination one molecule loses the elements of another small molecule t Elimination reactions give us a method for preparing compounds with double and triple bonds
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Ch. 3 - 9 v Examples C C H H CH 3 CH 3 C C H H H CH 3 CH 3 Br NaOMe MeOH heat + MeO H Na Br + C C C C H H Br H H Br NaNH 2 heat + 2 2 Na Br + H H H NH 2
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Ch. 3 - 10 v Rearrangements In a rearrangement a molecule undergoes a reorganization of its constituent parts Examples C C H 3 C H 3 C CH 3 CH 3 H C C C H H H CH 3 H 3 C H 3 C
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Ch. 3 - 11 1A. Homolysis and Heterolysis of Covalent Bonds v Homolysis A B radicals homolytic bond cleavage + A B
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Ch. 3 - 12 v Heterolysis A B ions A B heterolytic bond cleavage + A B + A B
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Ch. 3 - 13 Normally requires the bond to be polarized A B δ + δ ± Usually occurs with assistance A B Y δ + δ + B A Y
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Ch. 3 - 14 2. Acid–Base Reactions v Many of the reactions that occur in organic chemistry are either acid–base reactions themselves or they involve an acid–base reaction at some stage v Two classes of acid–base reactions are fundamental in organic chemistry Brønsted–Lowry Lewis acid–base reactions
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Ch. 3 - 15
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