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ch06 Solomons revised - Chapter6 Halides Createdby...

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Created by Professor William Tam & Dr. Phillis Chang Ch. 6 - 1 Chapter 6 Nucleophilic Substitution  and  Elimination Reactions  of Alkyl  Halides
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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. 6 - 2
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Ch. 6 - 3 1. Organic Halides v Halogens  are more electronegative than carbon C X δ + δ - X = Cl, Br, I
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Ch. 6 - 4 C F H H H C Cl H H H C Br H H H C I H H H C–X Bond Length ( Å ) 1.39 1.78 1.93 2.14 C–X Bond Strength (kJ/mol) 472 350 293 239 Carbon-Halogen Bond Lengths and Bond Strength increase decrease
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Ch. 6 - 5 Different Types of Organic Halides v Alkyl halides (haloalkanes) Cl Br I a 1o chloride a 2o bromide a 3o iodide Attached to 1 carbon atom C Attached to 2 carbon atoms C C Attached to 3 carbon atoms C C C sp3 C X
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Ch. 6 - 6 v Vinyl halides (Alkenyl halides) v Aryl halides v Acetylenic halides (Alkynyl halides) sp 2 X sp 2 X benzene or aromatic ring sp X
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Ch. 6 - 7 C X sp 3 δ + δ- Alkyl halides v Prone to undergo  Nucleophilic Substitutions (SN)   and  Elimination Reactions (E)  (the focus of this  Chapter) sp 2 X X X sp 2 sp v Different reactivity than alkyl halides, and do not undergo  SN  or  E  reactions
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Ch. 6 - 8 Nu + C X δ + δ - C Nu + X (nucleophile) (substrate) (product) (leaving group) The Nu donates an e  pair to the substrate The bond between C and LG breaks, giving both e  from the bond to LG The Nu  uses its e  pair to form a new covalent bond with the substrate C The LG gains the pair of e originally bonded in the substrate 2. Nucleophilic Substitution Reactions
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Ch. 6 - 9 v Two types of mechanisms 1st type: SN2 (concerted mechanism) R C Br R R δ + δ - HO R C R R Br HO δ - δ - transition state (T.S.) + Br - R C HO R R Timing of The Bond Breaking & Bond Making Process
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Ch. 6 - 10
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