Stereochemistry of the nucleophilic addition reaction
المؤلف:
University of Missouri System
المصدر:
Organic Chemistry ii
الجزء والصفحة:
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8-10-2020
2818
Stereochemistry of the nucleophilic addition reaction
Notice that in the course of the nucleophilic addition pictured above, the hybridization of the carbonyl carbon changes from sp2 to sp3, meaning that the bond geometry changes from trigonal planar to tetrahedral. It is also important to note that if the starting carbonyl is asymmetric (in other words, if the two R groups are not equivalent), then a new stereocenter has been created. The configuration of the new stereocenter depends upon which side of the carbonyl plane the nucleophile attacks from.
If the reaction is catalyzed by an enzyme, the stereochemistry of addition is tightly controlled, and leads to one specific stereoisomer – this is because the nucleophilic and electrophilic substrates are bound in a specific positions within the active site, so that attack must occur specifically from one side. If, however, the reaction occurs uncatalyzed in solution, then either side of the carbonyl is equally likely to be attacked, and the result will be a 50:50 racemic mixture.
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