N2 Mechanism - The WikiPremed MCAT Course"> S<sub class="intersub">N</sub>2 Mechanism - The WikiPremed MCAT Course



Integrated SequencePhysics Chemistry Organic Biology

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Work, Energy, and Power

Electricity

Thermochemistry

Chemical Thermodynamics and the Equilibrium State

Chemical Kinetics

Solutions

Reactions of Alkyl Halides

Primary carbocations are too high energy to allow for the SN1 mechanisms in any instance. The only substitution mechanism available to primary alkyl halides is SN2 substitution . The most favorable SN2 conditions occur with a primary alkyl halide in a polar aprotic solvent, but SN2 substitution can occur with a primary alkyl halide in other solvents as well. Polar aprotic solvents, like DMSO, are so favorable for SN2 substitution that they will even allow SN2 to occur with secondary alkyl halides. Polar aprotic solvents, like DMSO, are sufficient to stabilize the SN2 transition state, but they do not stabilize negatively charged nucleophiles so much that they do not react, unlike protic solvents.

Organic chemistry often uses kinetics and thermodynamic reasoning interchangeably, using a blanket expression such as 'making the reaction more favorable' for either case. We discussed above how a polar aprotic solvent such as DMSO makes for SN2 substitution more favorable for two reasons. First, the dielectric properties of a polar solvent allow charges to separate at lower voltage, so the polar aprotic solvent stabilizes the SN2 transition state. Secondly, being aprotic, the solvent will not overly stabilize the nucleophile. Which of these reasons a polar aprotic solvent makes SN2 substitution more favorable is based in chemical kinetics and which is based in chemical thermodynamics?

The MCAT is very fond of seeing if you are capable of separating kinetics from thermodynamics reasoning, so we are taking this as an example. The answer to the question is that lowering the energy of a transition state affects the kinetics of the reaction, making the reaction proceed more quickly, but raising the energy of reagents (less nucleophile stabilization) affects the thermodynamics of the reaction, pushing the equilibrium in the direction of products. Stabilization of the transition state would not change the position of equilibrium in itself, only the rate by which equilibrium is reached.




The Chemical Bond

Stereochemistry

Chemical Kinetics

Reactions of Alkyl Halides

SN2 substitution exhibits second order kinetics (first order in alkyl halide and first order in nucleophile). If increasing the concentration of the nucleophile does not change the reaction rate, the mechanism is not SN2 substitution but SN1 substitution.

Another important characteristic of SN2 is that it occurs with inversion of configuration. The incoming nucleophile attacks the molecule from the side opposite the leaving group, attacking the back lobe of the sp3 orbital containing the electron pair of the bond to the leaving group.








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