Chem 232 Lecture 12 - UIC Department of Chemistry - University of ...
Chem 232 Lecture 12 - UIC Department of Chemistry - University of ... Chem 232 Lecture 12 - UIC Department of Chemistry - University of ...
Halogen Addition Modification:Aqueous Solutions Give Halohydrinsbromohydrin• if the solvent for the reaction is changed to water,halohydrins are formed• since water is much more concentrated, it will add tohalonium ion intermediate faster than the halideUniversity of IllinoisUICat Chicago CHEM 232, Spring 2010Slide 28Lecture 12: February 1828
Ring Opening ofHalonium Ions is RegioselectiveH 3 CH 3 CBrHHBrH 3 CH 3 CBrHHBrOH 2H 3 CH 3 CHOHBrH HOH 2H 3 CH 3 CHOH 3 CHH 3 CBrH HHBrH• product is most substituted alcohol;least substituted halide• most substituted carbon is mostpartially positively charged intransition state = strongestelectrophile = water most attractedto that carbonUniversity of IllinoisUICat Chicago CHEM 232, Spring 2010Slide 29Lecture 12: February 1829
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Ring Opening <strong>of</strong>Halonium Ions is RegioselectiveH 3 CH 3 CBrHHBrH 3 CH 3 CBrHHBrOH 2H 3 CH 3 CHOHBrH HOH 2H 3 CH 3 CHOH 3 CHH 3 CBrH HHBrH• product is most substituted alcohol;least substituted halide• most substituted carbon is mostpartially positively charged intransition state = strongestelectrophile = water most attractedto that carbon<strong>University</strong> <strong>of</strong> Illinois<strong>UIC</strong>at Chicago CHEM <strong>232</strong>, Spring 2010Slide 29<strong>Lecture</strong> <strong>12</strong>: February 1829
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