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Unformatted text preview: Ad E 2 AND OTHER REACTIONS INVOLVING ALKENES Ad E 2 ADDITION REACTIONS--ALKENES • General mechanism--the π electrons in the alkene are the highest energy electrons in the molecule (i.e., they are in the HOMO). These electrons will attack an electrophile, leaving a positive charge (or a partial positive charge) on the most substituted carbon. Three variations are possible: one that involves a simple carbocation and one in which a halonium cation (bromonium cation) forms and dictates the stereochemical outcome of the reaction, and concerted reactions (hydroboration, epoxidation). • Note that alkenes are weak nucleophiles and will only react with strong electrophiles. These electrophiles include H 3 O + , HCl, HBr, HI, H 2 SO 4 , Cl 2 , Br 2 , I 2 , carbocations, BH 3 , R 2 BH, and peracids. • In reactions in which a positively charged intermediate is formed, the amount and nature of the nucleophiles present must be considered to understand and/or predict the outcomes of the reactions....
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