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Unformatted text preview: both enantiomers of the product are formed in equal amounts. In other words, why is this reaction nonstereoselective ? A good explanation should require no more than a sentence or two!!! The carbocation intermediate has trigonal planar geometry at the positively charged carbon atom. The iodide anion can react from either side of this plane with equal likelihood, so both possible stereochemical configurations of the new chiral center are formed in equal amounts. C C CH 3 CH 2 CH 2 CH 3 H CH 3 H I C CH 2 CH 3 I CH 3 CH 3 CH 2 CH 2 C C H H CH 3 CH 3 CH 2 CH 2 CH 3 I trigonal planar geometry at the cationic center the other enantiomer is formed when I-attacks from the other side of the plane...
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- Spring '05