To develop a correlation between the structure of an alkyl halide and its preferred substitution mechanism and to use this correlation to make predictions about an unknown alkyl halide. Use the models available by clicking on the boxed items and the other information in the table to predict the SN1 and SN2 reactivities of each compound. Not all of the information provided is expected to be useful.
| Alkyl Halide | 2-D Structure | 3-D Structure | Energies (a.u.) | |
|---|---|---|---|---|
| Alkyl Halide | Alkyl Cation | |||
| 1-Bromobutane | | -2716.121 | -155.531 | |
| 1-Chlorobutane | | -613.253 | -155.531 | |
| 2-Bromobutane | | -2716.123 | -155.547 | |
| 2-Chlorobutane | | -613.255 | -155.547 | |
| 2-Chloro-2-methylpropane | | -613.261 | -155.564 | |
| Bromocyclohexane | | -2792.603 | -232.045 | |
| Bromobenzene | | -2789.106 | -228.464 | |
| Benzyl Chloride | | -725.053 | -267.380 | |
| Bromodiphenylmethane | | -3056.183 | -495.676 | |
| Halide | Electronegativity | Electron Affinity | Anion Energy | pKa of Conjugate Acid |
|---|---|---|---|---|
| Chlorine | 3.0 | 3.61 | -457.444 | -2.2 |
| Bromine | 2.8 | 3.36 | -2560.300 | -4.7 |
All energies provided on this page were calculated using the Ab Initio package available in Spartan. Calculations were performed at the 3-21G* level and should be trusted accordingly.
Abby Parrill and Dr. Jacquelyn Gervay
The Department of Chemistry
The University of Arizona
Tucson, AZ 85721
Please contact Abby Parrill at abby@mercury.aichem.arizona.edu with problems and comments.