ch06 Solomons revised

ch06 Solomons revised - Created by Professor William Tam...

Info iconThis preview shows pages 1–10. Sign up to view the full content.

View Full Document Right Arrow Icon

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: Created by Professor William Tam & Dr. Phillis Chang Ch. 6 - 1 Chapter 6 Nucleophilic Substitution and Elimination Reactions of Alkyl Halides 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 Ch. 6 - 3 1. Organic Halides v Halogens are more electronegative than carbon C X δ + δ- X = Cl, Br, I 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 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 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 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 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 Ch. 6 - 9 v Two types of mechanisms ● 1st type: SN2 (concerted mechanism)...
View Full Document

This note was uploaded on 01/16/2012 for the course PSYCH 373 taught by Professor Marthafaircloth during the Spring '09 term at Campbell University .

Page1 / 105

ch06 Solomons revised - Created by Professor William Tam...

This preview shows document pages 1 - 10. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online