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Unformatted text preview: must be able to accept/stabilize the electron density in the C—X bond (heterolytic bond cleavage). What makes a good leaving group? 3. Nu – a nucleophile; the nucleophile must contain a lone pair or a pi bond, but it does not necessarily have to be negatively charged. (Charged nucleophiles react more easily than neutral ones.) Page 3 of 24 C341/Fall 2011 1. Chapter 7: Nucleophilic Substitution Reactions Alkyl Halides Which alkyl halide C—X bond will react fastest? Why? Page 4 of 24 C341/Fall 2011 2. Chapter 7: Nucleophilic Substitution Reactions The SN2 Mechanism What is the rate law for this reaction? What type of experiment could you run in the lab to test whether this mechanism is valid? How might we use stereochemistry to support the SN2 mechanism for the following reaction? Page 5 of 24 C341/Fall 2011 Chapter 7: Nucleophilic Substitution Reactions SN2 & Sterics Less sterically‐hindered electrophiles react more readily under SN2 conditions. Sterics plays a part at the reactive carbon (α‐carbon), but also at the β‐carbon. H
H H3C H Page 6 of 24 X
H C341/Fall 2011 Chapter 7: Nucleophilic Substitution Reactions Put the following reactants in order of ease of reacting via an SN2 reaction (1‐4; 1 = fastest, 4 = slowest) Br...
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