Selectivity and specificity in organic reactions

1. Selectivity:
The selective formation of one product isomer over all possible isomers or one product is
formed in higher percentage over the other.

2. Specificity:
Specific formation of only one product isomer in 100 percent ratio out of all possible isomers.

In summary selective implies that there are factors which favor one product isomer over
the other while specific is usually a sign that there is something inherent to the mechanism
that leads to only one product.

Selectivity and specificity in organic

reactions

Selectivity Specificity

Stereoselectivity Regioselectivity Chemoselectivity Stereospecificity

Enantioselectivity
Regiospecificity

Diastereoselectivity
Chemospecificity

1
Stereoselectivity:
• A stereoselective reaction is a reaction
which involves preferential formation of
one stereoisomer.
• In stereoselective reaction there is a choice
of pathway and that stereoisomer is formed
preferably or in higher percentage whose
pathway being more favorable.
• Selectivity of the reaction pathway depends
on differences in steric effects and
electronic effects
Regioselectivity: (Latin-Regio means
region or direction.)
• Formation of one regioisomer/ positional
isomer in higher percentage in relation to
the other possible regioisomers.
Chemoselectivity:
Reaction that operates predominantly on one
functional group or reaction in which reagent
reacts selectively with one functional group in
the presence of all other functional groups in
the structure of the molecule. The resulting
chemoselective product is formed in higher
percentage.
Chemoselectivity is the preferential outcome of
a chemical reaction over a set of possible
alternative reactions.
Stereospecificity:
• A stereospecific reaction is a reaction
which gives only one stereoisomeric
product.
• In stereospecific reaction only one specific
pathway is allowed.
• The stereochemistry or configuration of the
product depends uniquely on the
configuration of the catalyst or the reactant.
Regiospecificity:
• Specific formation of only one regioisomer
in 100 percent ratio.
Chemospecificity:
In chemospecific reaction reagent react
specifically with one functional group in the
presence of all other functional groups giving
rise to 100 percent of only one specific product.