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chap6solomons - Chapter6 AlkylHalides Createdby...

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Created by Professor William Tam & Dr. Phillis Chang Ch. 6 - Chapter 6 Chapter 6 Nucleophilic Substitution Nucleophilic Substitution     and  and  Elimination Reactions Elimination Reactions  of   of  Alkyl Halides Alkyl Halides
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About The Authors 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 -
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Ch. 6 - 1. Organic Halides Halogens  are more electronegative  than carbon C X δ + δ - X = Cl, Br, I
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Ch. 6 - 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 Carbon-Halogen Bond Lengths and Bond Strength and Bond Strength increase decrease
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Ch. 6 - C h l o r i d e -23.8 13.1 78.4 68 69 51 G r o u p Me Et Bu s Bu i Bu t Bu F l u o r i d e -78.4 -37.7 32 - - 12 B r o m i d e 3.6 38.4 101 91.2 91 73.3 I o d i d e 42.5 72 130 120 119 100(dec) . Physical Properties of Organic Halides: Physical Properties of Organic Halides: Boiling Point (bp/ Boiling Point (bp/     C) C)
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Ch. 6 - C h l o r i d e 0.92 0.91(15) 0.89 0.87 0.87 0.84 G r o u p Me Et Bu s Bu i Bu t Bu F l u o r i d e 0.84(-60) 0.72 0.78 - - 0.75(12) B r o m i d e 1.73(0) 1.46 1.27 1.26 1.26 1.22 I o d i d e 2.28 1.95 1.61 1.60 1.60 1.57(0) Physical Properties of Organic Halides: Physical Properties of Organic Halides: Density ( Density ( ρ ρ ) )
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Ch. 6 - Different Types of Organic Halides Different Types of Organic Halides Alkyl halides (haloalkanes) 1 o   chloride 3 o   iodide Attached to 1 carbon atom C Attached to 2 carbon atoms C C Attached to 3 carbon atoms C C C sp 3 C X
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Ch. 6 - Vinyl halides (Alkenyl halides) Aryl halides Acetylenic halides (Alkynyl halides) sp 2 X sp 2 X benzene or aromatic ring sp X
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Ch. 6 - C X sp 3 δ + δ- Alkyl halides Prone to undergo  Nucleophilic  Substitutions (S N )
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