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columbia大学有机化学课件 （三十八）
7.13 Chemical Reactions That Produce Diastereomers Stereochemistry of Addition to Alkenes In order to know understand stereochemistry of product, you need to know two things: (1) stereochemistry of alkene (cis or trans; Z or E) (2) stereochemistry of mechanism (syn or anti) Bromine Addition to trans-2-Butene Fig. 7.14 (p 284) anti addition to trans-2-butene gives meso diastereomer Bromine Addition to cis-2-Butene Fig. 7.15 (p 285) anti addition to cis-2-butene gives racemic mixture of chiral diastereomer Epoxidation of trans-2-Butene Problem 7.17 (p 285) syn addition to trans-2-butene gives racemic mixture of chiral diastereomer Epoxidation of cis-2-Butene Problem 7.17 (p 285) syn addition to cis-2-butene gives meso diastereomer Stereospecific reaction of two stereoisomers of a particular starting material, each one gives different stereoisomeric forms of the product related to mechanism: terms such as syn addition and anti addition refer to stereospecificity Stereospecific reaction Stereoselective reaction a single starting material can give two or more stereoisomeric products, but gives one of them in greater amounts than any other 7.14 Resolution of Enantiomers separation of a racemic mixture into its two enantiomeric forms Strategy Strategy Strategy Strategy 7.15 Stereoregular Polymers atactic isotactic syndiotactic Atactic Polypropylene random stereochemistry of methyl groups attached to main chain (stereorandom) properties not very useful for fibers etc. formed by free-radical polymerization Isotactic Polypropylene stereoregular polymer; all methyl groups on same side of main chain useful properties prepared by coordination polymerization under Ziegler-Natta conditions Syndiotactic Polypropylene stereoregular polymer; methyl groups alternate side-to-side on main chain useful properties prepared by coordination polymerization under Ziegler-Natta conditions 7.16 Stereogenic Centers Other Than Carbon Silicon silicon, like carbon, for
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