The SN2 reaction involves three things interacting:
- A nucleophile (a Lewis base that is using an electron pair
to form a new bond);
- A leaving group (an atom or group that will pull an
existing bonding electron pair away from the reaction site)
- The substrate carbon, on which the leaving group is being
replaced with the nucleophile.
The structures below are predictions based on an MO calculation.
Note several things:
- There is an activation barrier of about 10.6 kcal/mol (45 kJ/mol).
- The reaction is exothermic by about 42.5 kcal/mol (178 kJ/mol).
- The transition state structure is symmetric; the carbon is
being inverted.
- The bond lenghts in the transition state are all longer
than in either reactant or product--evidence of partial bonding.
- The nucleophile (cyanide) approaches from the opposite side
of the molecule from where the bond to the leaving group (bromide) is
being broken. (There is an MO explanation for this: the
lone pair on the nucleophile interacts with the antibonding MO for the
C-Br bond.) Go back to the top and click "Stereochemuistry" to see how the stereochemistry of a secondary center is affected.
The details will vary, but all SN2 reactions follow this
general motif.
Because this is a single step reaction that brings nucleophile and
substrate together, the rate is second order overall--first order in
nucleophile, first order in substrate:
Rate = k[MeBr][-CN]
The SN2 terminology means Substitution,
Nucleophilic, 2nd order.
Several things control the rate constant (and therefore the rate):
-Strength of the nucleophile.
-Leaving group ability.
-Steric hindrance of the reacting carbon
-Solvent stabilization of ionic reactants, products or transition
states.
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