Ch_322a_6.014 - Because carbocations have a trigonal planar...

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Stereochemistry of the S N 1 Reaction Because carbocations have a trigonal planar geometry, they possess a plane of symmetry and are achiral . Therefore, a racemic form of a chiral product is predicted in reactions that involve carbocation intermediates. C R 1 R 2 R 3 X A General Scheme chiral -X - C R 1 R 2 R 3 + achiral (plane of symmetry) O-H H : : H-O H : : C R 1 R 2 R 3 O-H H : + C R 1 R 3 R 2 H-O H : + S N 1 chiral chiral There are equal probabilities of reaction at the two faces of the carbocation. The two oxonium ions formed in equal amounts are enantiomers . A racemic form of the product is necessarily produced.
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Racemization The reaction of an optically active starting material that yields a racemic form of a chiral product is said to proceed with racemization . The S N 1 reaction of an optically active substrate necessarily produces a racemic form of a chiral product, so the stereochemical course of such a reaction is racemization.
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