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 ...
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Mechanism <strong>of</strong> HydroborationH 2 BHCH 3H 2 BHCH 3 CH 3CH 3H 2 BCH 3Why this regioselectivity?H 2 Bnot<strong>University</strong> <strong>of</strong> Illinois• Syn Addition: B and H atoms add to same side(face) <strong>of</strong> C-C double bond at same time• hydride (H:) adds to most substituted carbon• boron adds to least substituted carbon• this is NOT a PROTONATION<strong>UIC</strong>at Chicago CHEM <strong>232</strong>, Spring 2010Slide 13<strong>Lecture</strong> <strong>12</strong>: February 18Note that although the borane generated upon monohydroboration <strong>of</strong> methylcyclopentene is itselftrans-substituted, the hydroboration remains a syn-addition. In other words, it is the BH2 groupand beta-hydrogen on the carbon bearing the methyl group which are in a syn relationship.13
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