Lesson20 - Stereochemistry of the[SN2 Pathway...

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Stereochemistry of the [S N 2] Pathway The S N 2 reactions proceeds with _______ of configuration. Stereospecific or Stereoselective? inversion Stereospecific Reaction : A reaction in which the stereochemistry of the reactant completely determines the stereochemistry of the product without any other option. Stereoselective Reaction : A reaction in which there is a choice of pathway, but the product stereoisomer is formed preferentially because its reaction pathway is more favorable than the others available.
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Stereochemistry of the [S N 1] Pathway The nucleophile will attack both faces of the planar carbocation with equal probability resulting in a racemic mixture . planar carbocation (achiral) Starting with a single enantiomer http://www.chemtube3d.com/
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The [E2] reaction pathway has very specific requirements: There must be ________________ among the orbitals in which σ bonds are made/broken and π bonds are made. continuous overlap Stereochemistry of the [E2] Pathway
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Conformational Requirements of [E2] Elimination (1) –X and –H oriented anti-periplanar (2) –X and –H oriented syn-periplanar For steric reasons, the preferred pathway for [E2] elimination is through (1). The double bond geometry depends on which pathway is followed. Consider the following example: The carbon atoms smoothly rehybridize from sp 3 to sp 2 http://www.chemtube3d.com/EliminationE2stereospecific.html Here’s another example:
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