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ch08 - Chapter8 AlkenesandAlkynesII AdditionReactions...

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Created by Professor William Tam & Dr. Phillis Chang Ch. 8 - Chapter 8 Chapter 8 Alkenes and Alkynes II: Alkenes and Alkynes II: Addition Reactions Addition Reactions
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Ch. 8 - 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.
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Ch. 8 - C C E Nu E C C Nu + 1. Addition Reactions of Alkenes
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Ch. 8 - 1A. 1A. How To  How To  Understand Additions  Understand Additions  to Alkenes to Alkenes This is an addition reaction:  E Nu   added across the double bond C C E Nu E C C Nu + Bonds broken Bonds formed π -bond σ -bond σ -bonds
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Ch. 8 - Since p bonds are formed from the  overlapping of  π  orbitals,  π  electron  clouds are above and below the plane  of the double bond C C π  electron  clouds
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Ch. 8 - Electrophilic electron seeking C=C and C π  bonds are  particularly susceptible to  electrophilic reagents  (electrophiles) Common electrophile H + , X +  (X = Cl, Br, I), Hg 2+ ,  etc.
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Ch. 8 - In an electrophilic addition, the  π   electrons seek an electrophile,  breaking the  π  bond, forming a  σ  bond  and leaving a positive charge on the  vacant  π  orbital on the adjacent  carbon.  Addition of B  to form a  σ  bond  provides an addition product
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Ch. 8 - C C A C C E C C Nu Nu E Nu δ + δ - 2. Electrophilic Addition of Hydrogen Halides to Alkenes:  Mechanism and Markovnikov’s Rule Mechanism
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Ch. 8 - C C E Mechanism Sometimes do not go through a  “free carbocation”, may go via
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Ch. 8 - 1 C C H H H H E Nu E C C H H H H E C C H H H H E C C H H H H Nu E C C H H H H Nu Nu same  as same  as Markovnikov
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