ChemActivity26_oxidation_and_reduction_reactions_key - 1...

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1 ChemActivty 26: Electrophilic Addition: Other Reactions Involving Addition of Oxygen Model 1: Hydration of Alkenes The addition of water to an alkene is called hydration and results in formation of an alcohol. There are several reagents that result in hydration of an alkene: each method gives an alcohol but with different regio- and stereochemical outcomes. 2. H 2 O 2 , HO H 2 SO 4 H 2 O 1. Hg(OAc) 2 , H 2 O 2. NaBH 4 1. BH 3 OH OH OH H 1. Identify the reactions shown in Model 1 as hydroboration, oxymercuration and acid catalyzed hydration. 2. Label each product from Model 1 as Markovnikov or anti-Markovnikov addition. 3. Indicate whether each reaction in Model 1 occurs to give syn addition, anti addition or both. Model 2: Epoxidation of Alkenes The reaction of an alkene with a peroxy acid results in formation of an epoxide as shown below. The mechanism is concerted. R + O R' OOH O R + O R' OH peroxy acid epoxide 4 . A peroxyacid has the general formula of RCO 3 H (the R group can be anything). (a). Draw a Lewis structure for a peroxy acid. (b). Draw resonance structures for the peroxy acid, above. (c). Given that an O-O bond is weak, predict which oxygen of the peroxyacid is likely to act as the electrophile.
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2 (d). Draw the reaction of the alkene with the electrophilic oxygen using curved arrows to show electron movement (consider for now that the reaction is stepwise and you are just showing the first step). Does the leaving group (after breaking the O-O bond) help explain why one oxygen is
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ChemActivity26_oxidation_and_reduction_reactions_key - 1...

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