ch07 - Chapter7 AlkenesandAlkynesI ofAlkylHalides Createdby...

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Created by Ch. 7 - 1 Chapter 7 Alkenes and Alkynes I: Properties and Synthesis. Elimination Reactions of Alkyl Halides
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Ch. 7 - 2 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.
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Ch. 7 - 3 2. The ( E ) - ( Z ) System for  Designating Alkene Diastereomers v Cis - Trans  System Useful for 1,2-disubstituted alkenes Examples: Cl Br H H Cl H Br H (1) vs trans  - 1-Bromo- 2-chloroethene cis  - 1-Bromo- 2-chloroethene
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Ch. 7 - 4 Examples H H (2) vs trans  - 3-Hexene cis  - 3-Hexene H H Br (3) vs trans  - 1,3- Dibromopropene cis  - 1,3- Dibromopropene Br Br Br
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Ch. 7 - 5 Cl Br CH 3 H e.g. cis  or  trans ? Cl is  cis  to CH3 and  trans  to Br v (E)  -  (Z)  System Difficulties encountered for trisubstituted and tetrasubstituted alkenes
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Ch. 7 - 6 v The Cahn-Ingold-Prelog  (E)  -  (Z)  Convention The system is based on the atomic number of the attached atom  The higher the atomic number, the higher the priority
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Ch. 7 - 7 v The Cahn-Ingold-Prelog  (E)  -  (Z)   Convention (E)  configuration – the highest priority  groups are on the  opposite  side of the  double bond t E  ” stands for “ entgegen ”; it means  opposite ” in German (Z)  configuration – the highest priority  groups are on the  same  side of the  double bond t ” stands for “ zusammer ”; it means  together ” in German
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Ch. 7 - 8 On carbon  2 :  Priority of  Br  >  C On carbon  1 :  Priority of  Cl  > H highest priority groups  are  Br  (on carbon 2)  and  Cl  (on carbon 1) Cl Br CH 3 H 2 1 Examples
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ch07 - Chapter7 AlkenesandAlkynesI ofAlkylHalides Createdby...

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