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Brønsted Acid Additions

The stereoselectivity of Brønsted acid addition is sensitive to experimental conditions such as temperature and reagent concentration. The selectivity is often anti, but reports of syn selectivity and non-selectivity are not uncommon. Of all the reagents discussed here, these strong acid additions (E = H in the following equation) come closest to proceeding by the proposed two-step mechanism in which a discrete carbocation intermediate is generated in the first step. Such reactions are most prone to rearrangement when this is favored by the alkene structure.

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