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The concepts of syn and anti addition are used to characterize the different reactions of organic chemistry by reflecting the stereochemistry of the products in a reaction. The type of addition that occurs depends on multiple different factors of a reaction, and is defined by the final orientation of the substituents on the parent molecule .
syn/anti peri/clinal. a torsion angle between 0° and ±90° is called syn (s) a torsion angle between ±90° and 180° is called anti (a) a torsion angle between 30° and 150° or between −30° and −150° is called clinal (c) a torsion angle between 0° and ±30° or ±150° and 180° is called periplanar (p)
When the single bond between the two centres is free to rotate, cis/trans descriptors become invalid. Two widely accepted prefixes used to distinguish diastereomers on sp³-hybridised bonds in an open-chain molecule are syn and anti. Masamune proposed the descriptors which work even if the groups are not attached to adjacent carbon atoms.
Anti-periplanar geometry will put a bonding orbital and an anti-bonding orbital approximately parallel to each other, or syn-periplanar. Figure 6 is another representation of 2-chloro-2,3-dimethylbutane (Figure 5), showing the C–H bonding orbital, σ C–H, and the C–Cl anti-bonding orbital, σ* C–Cl, syn-periplanar.
2006-11-30T05:51:12Z E kwan 1295x258 (9602 Bytes) syn vs anti convention; Uploaded with derivativeFX. Captions. English. Add a one-line explanation of what this file ...
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The disposition of the formed stereocenters is deemed syn or anti, depending if they are on the same or opposite sides of the main chain: Syn and anti products from an aldol (addition) reaction. The principal factor determining an aldol reaction's stereoselectivity is the enolizing metal counterion.
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