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Why trans-alkene on addition only gives meso compounds?

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You think of the molecules when the addition does take place. Think of the orientation of the molecules. For example, consider in cis, both Me are on same side, so in product both are wedged. Picture how the bond is transforming mentally. You will see, that trans must give meso. read more

Syn addition results in formation of a compound with a plane of symmetry- Meso Compound. Anti addition results in formation of two enantiomers- Racemic Mixture. Trans: Anti addition results in formation of a Meso compound. Syn addition results in formation of enantiomers- Racemic Mixture. read more

In contrast, the addition of bromine to trans-butene as shown in Fig. 2 yields a chiral intermediate bromonium ion possessing no mirror plane. However, in this special case the products (2S,3R)-2,3-dibromobutane and (2R,3S)-2,3-dibromobutane are meso compounds and therefore identical. read more

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