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Ch_322a_6.05 - features of this nucleophilic substitution...

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A Mechanism for the S N 2 Reaction The Hughes-Ingold Mechanism for the S N 2 Reaction In their mechanism, the nucleophile attacks the carbon center on the side opposite the leaving group. As overlap develops between the orbital with the electron pair of the nucleophile and the antibonding orbital of the substrate, the bond between the carbon and the leaving group weakens. Nu : - C L : Nu C : L : weakening bond developing bond In 1937 Edward Hughes and Sir Christopher Ingold proposed a mechanism to explain the second order kinetics and other important
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Unformatted text preview: features of this nucleophilic substitution reaction that were known at that time. The Walden Inversion This backside attack by the nucleophile results in an inversion of absolute configuration at the carbon center that is called a Walden inversion after Paul Walden (1863-1957) who accidently discovered the first such inversion of configuration at carbon in 1896. C L Nu:-+ Nu C + L:-* * The Walden inversion is a key characteristic of the S N 2 mechanism....
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