Solutions_Manual_for_Organic_Chemistry_6th_Ed 172

Solutions_Manual_for - 8-17 continued Enantiomers of chiral products are also produced but not shown Br � Br(a Br-Br 8-18 H HC Br)1-J,H H Br Br H

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Unformatted text preview: 8-17 continued Enantiomers of chiral products are also produced but not shown. Br .. � + : Br: (a) Br-Br 8-18 H HC Br )1-J,H H Br Br H CH3 �Br + \� H + Br Br + H / �HCH3 "' H\'CH3 Br Br CH3 CH3 2R,3S ID ENTICAL-MESO 2R,3S CONCLUSION: anti addition of a symmetric reagent to a symmetric cis-alkene gives racemic product, while anti addition to a trans-alkene gives meso product. (We will see shortly that syn addition to a cis­ alkene gives meso product, and syn addition to a trans-alkene gives racemic product. Stay tuned.) + ENANTIOMERIC � TRANS \ ( B! H" CH �"CH3 U " ,U H '/H3 "" "'CH+ \Br/ bromide attack on thisthe bame resultsion gives C1V\11 3 + s romonium a Be nucleophile could :Br: OR :Br: attack at either carbon �------� �--------- , �( t ' •• J + (b) (c) (Hex) + Bromide will attack the other carbon of the bromonium ion as well. + 0. � Br\ +) Br-Br --- , U - ___ '>---f/ .. "'/ '" Br "Et It��" ' Hex:Br: HEt 1 H" � Br 0 Br "'Br �e1-I 165 ...
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This note was uploaded on 02/27/2010 for the course CHEM 140 taught by Professor Wade during the Spring '10 term at Whitman.

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