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9) The stereoselectivity of the reaction appears to be limited to the internal double-bond isomer. Thus bromination of l-hepten-3-ol produces a 2:1 mixture of dibromo diastereomers under a variety of conditions including aqueous base. Similar results (although attributed to competing reactions of direct closure of the hydroxy bromonium ion and epoxide formation via the dibromide and not to addition of bromine to the two diastereotopic faces of the double bond) have been reported for 2-methyl-l-buten-3-ol.4(10) Alfred P. Sloan Foundation Fellow, 1978-1982 Recipient of a President's Undergraduate Fellowship.