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Reaction Summary Table Including Mechanisms and Reactants, Products

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CHEM 266
Steve Forsey

nu atk after boron big bind to least ANTI ADDITIONRearrangement possible NO REARRANGEMENTNotes proton transfer to form most stable c 3 halogen can add from topbottom diastereomers formmost stable c formed rearrangement possible occur with DILUTE acid solvent conc acid solvent cause dehydration Reverse reaction hydration addition favoured at lower temp but reagents present dominate temperaturedehydration indicated by high temp CONC acid usage REARRANGEMENT POSSIBLE 1formation of cyclo makes bigger delta positive charge on 3 C 2 antiMarkovnikovSyn additionsubbed C easierregioselective stereoselective can form racemic pair enantiomers if chiral carbon formmarkovnikov selectivitymost subbed carbon h added to least subbed C backside attack Mechanism Form carbocation from proton transfer nucleophilic atk 1Form carbocation from Proton Transfer to alkene 2nucleophilic atk by water 3proton transfer from water remove h from alkane 1Alcohol protonated 2 water leaves carbocation intermediate form 3elimination rxn form alkene 1nu atk on Hg and Hg atk alkene bond to form cyclo 2H2O nu atk on more stable C3H2O proton transfer w another H2O to neutralize form H3O 4Hg replaced by H 1alkene nu atk on BH4 boron bind to least subbed C H bind to most subbed C 2bond between B andbound H breaks 3BH2 replace with OH Aaron Tai CHEM 266 Reaction Summary Table Electrophile Hydrogen then protonated alkene H then Carbocation then water bonded to alkane mercury BH3 alkane Nucleophile Alkene then halogenAlkene then water then wateralkene Alkene then HReaction Hydrohalogenation HydrationDehydration Oxymercurationdemercuration Hydroboronationoxidation
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