Chapter 6.2 Lecture Notes

Chapter 6.2 Lecture Notes - Chapter 6 14 The Effects of...

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Unformatted text preview: Chapter 6 - 14 The Effects of Nucleophiles S N 1 Reaction Rate does not depend on nucleophile. S N 2 Reaction Rate is directly proportional to the concentration of nucleophile. Stronger nucleophiles also react faster. Negative charge is better than neutral conjugate acid. When comparing nucleophiles with the same atom, nucleophilicities parallel basicities Larger nucleophiles are more polarizable and can donate more electron density ---> higher polarizability. Chapter 6 - 15 Polarizability- Able to make polar when necessary.- Small atoms are not polarizable.- Large atoms are polarizable, make it more nucleophilic I F more dispersed---> less stressed compact ---> more stressed I F more electron density at the interface---> react faster less electron density at the interface---> react slowly In general (solvent effect can change the order, cf . solvent effect) , more polarizable, more nucleophilic, and also better leaving group Chapter 6 - 16-The best leaving groups are weak bases which are relatively stable. OH- < H 2 O as a leaving group The Nature of the Leaving Group-Leaving group ability of halides opposite to basicity: Why? ---> Polarizability.- Other very weak bases which are good leaving groups: <--- strong base <--- weak base Chapter 6 - 17 There are three types of solvents....
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Chapter 6.2 Lecture Notes - Chapter 6 14 The Effects of...

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