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Stereoselective & Stereospecific Reactions

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STEREOSELECTIVE & STEREOSPECIFIC REACTIONS

Stereochemistry plays an important role in chemical reactions. There are many reactions of chiral
and achiral molecules and the formation of product in such case is controlled by stereochemical
consideration such as regioselective, Stereoselective and stereospecific reactions.
Stereoselective reactions: Stereoselectivity is the property of a chemical reaction that yields an
unequal mixture of isomers from a single reactant. It may be partial, where the formation of one
isomer is favoured over the other, or it may be total where only one isomer is formed.
Stereospecific reactions: Stereospecificty is the property of a reaction mechanism that yields
different isomeric products from different isomeric reactants, or which operates on only one (or a
subset) of the isomers. That is, a given isomer leads to one product while another isomer leads to
the opposite product.

Few important points:


(i) All stereospecific reactions are necessarily stereoselective, but the vice-versa is not true.
(ii) A stereospecific mechanism specifies the stereo-chemical outcome of a given reactant, whereas
a stereoselective reaction selects products from those made available by the same, non-specific
mechanism acting on a given reactant. A consequence of these definitions is that if a reaction is
carried out on a compound that has no stereosisomers, it cannot be stereospecific, but
stereoselective.
(iii) Stereospecificity is the property of a reaction mechanism, whereas stereoselectivity is the
property of reactant.

BP 401T (Pharm. Organic Chemistry-III), by Prof. Asif Husain Page 1


BP 401T (Pharm. Organic Chemistry-III), by Prof. Asif Husain Page 2
BP 401T (Pharm. Organic Chemistry-III), by Prof. Asif Husain Page 3

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