Interpretation:
The mechanism for the formation of chiral glycol from 1,2-chlorhydrin including formal charges and movement of electrons is to be proposed.
Concept introduction:
Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon, or a functional group, is substituted by any other functional group is called substitution reaction.
Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.
Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated bonds by addition of molecules.
Nucleophilic substitution happens by two different mechanisms:
The
In the rate determining step, leaving group generates a carbocation intermediate.
Carbocation intermediated then undergoes a rapid reaction with nucleophile.
Forms a racemic mixture.
The
In the rate determining step, nucleophile approaches the carbon from the side directly opposite to the leaving group.
The
This back side attack of nucleophile leads to inversion of configuration.
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Organic Chemistry
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- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning