Ch05_Handout5 - Reaction Stereochemistry In s e v e r a l o...

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1 Reaction Stereochemistry Reaction Stereochemistry In several of the reactions presented in this chapter, chiral centers are created Where one or more chiral centers are created, is the product one enantiomer and, if so, which one? a pair of enantiomers as a racemic mixture? a meso compound? a mixture of stereoisomers? Br B r H 2 C C (CH 3 ) 2 CH CH 2 CH 3 H B r C (CH 3 ) 2 CH H 3 C CH 2 CH 3 Br ( S ) C (CH 3 ) 2 CH H 3 C CH 2 CH 3 Br ( R ) Stereochemistry of HX Stereochemistry of HX Addition Addition In an addition reaction to an alkene that generates a chiral center, the R and S enantiomers are formed in equal amounts, and the product is a racemic mixture
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2 Reaction Stereochemistry Reaction Stereochemistry We saw that bromine adds to 2-butene to give 2,3-dibromobutane two stereoisomers are possible for 2-butene; a pair of cis,trans isomers three stereoisomers are possible for the product; a pair of enantiomers and a meso compound if we start with the cis isomer, what is the stereochemistry of the product? if we start with the trans isomer, what is the stereochemistry of the product? CH 3 CH=CHCH 3 Br 2 CH 2 Cl 2 CH 3 CH-CHCH 3 Br Br 2,3-Dibromobutane 2-Butene + Bromination of Bromination of -2-Butene -2-Butene reaction of -2-butene with bromine forms bridged bromonium ions which are meso and identical
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3 Bromination of Bromination of cis -2-Butene -2-Butene
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This note was uploaded on 12/09/2010 for the course CHM 265 taught by Professor Savinov during the Fall '10 term at Purdue University-West Lafayette.

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Ch05_Handout5 - Reaction Stereochemistry In s e v e r a l o...

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