In this type of reaction, a nucleophile reacts with haloalkane (the substrate) having a partial positive charge on the carbon atom bonded to halogen. A substitution reaction takes place and halogen atom, called leaving group departs as halide ion. Since the substitution reaction is initiated by a nucleophile, it is called nucleophilic substitution reaction

Path Limitations There are three requirements for the S N 2 reaction. In order to be pushed out, the leaving group must be at least fair, usually good. The nucleophile also must be reactive enough to push out the leaving group. Finally, the back side of the tetrahedral carbon attacked must be accessible to the nucleophile and not blocked by other groups.

The hydroxide ion is a good nucleophile since the oxygen atom has a negative charge and a pair of unshared electrons. The carbon atom is electrophilic since it is bound to a (more electronegative) halogen, which pulls electron density away from the carbon, thus polarizing the bond with carbon bearing partial positive charge and the halogen bearing partial negative charge. The nucleophile is attracted to the electrophile by electrostatic charges. The nucleophile attacks the electrophilic carbon through donation of 2 electrons. Carbon can only have a maximum of 8 valence electrons, so as the carbon nucleophile bond is forming, then the carbon-leaving group bond must be breaking. Iodide is the leaving group since it leaves with the pair of electrons that once bound it to carbon.

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