Substitution Reactions - SN1 and SN2 Mechanisms: Crash Course Organic Chemistry #21

We’ve already learned a bit about substitution reactions in organic chemistry and the two different paths they can follow: SN1 and SN2. In order to better predict the products of a substitution reaction and understand how they work, we need to be able to figure out which mechanism a reaction is likely to follow. In this episode of Crash Course Organic Chemistry, we’ll deepen our knowledge of substitution reactions by looking at factors like substrate structure and reaction conditions to determine whether SN1 or SN2 is the more likely mechanism.

Episode Sources:
Brookes, P., Lawley, P.D. “The Reaction of Mono-and Di-Functional Alkylating Agents with Nucleic Acids,” , Biochem. J., 1961, 80, 496-503.
Copley, Shelley, D., “Microbial dehalogenases: Enzymes recruited to convert xenobiotic substrates,” Current opinion in Chemical Biology, 1998, 2, 613-617.
Janssen, D. B., Scheper, A., Dijkhuizen, L, Witholt, B., “Degradation of halogenated aliphatic compounds by Xanthobacter autotrophicus GJ10,” Applied and Environmental Microbiology, 1985, 29, 673-677.
Silberstein, M., Dambrosky, J., Vajda, S., “Exploring the binding sites of the haloalkane dehalogenase Dhla from Xanthobacter autotrophicus GJ10,” Biochemistry, 2007, 46,9239-9249.
McCoy, M., “Dry Cleaning Dreams,” Chemistry and Engineering News, 2005, 83(46), 19-22.

Series Sources:
Brown, W. H., Iverson, B. L., Ansyln, E. V., Foote, C., Organic Chemistry; 8th ed.; Cengage Learning, Boston, 2018.
Bruice, P. Y., Organic Chemistry, 7th ed.; Pearson Education, Inc., United States, 2014.
Clayden, J., Greeves, N., Warren., S., Organic Chemistry, 2nd ed.; Oxford University Press, New York, 2012.
Jones Jr., M.; Fleming, S. A., Organic Chemistry, 5th ed.; W. W. Norton & Company, New York, 2014.
Klein., D., Organic Chemistry; 1st ed.; John Wiley & Sons, United States, 2012.
Louden M., Organic Chemistry; 5th ed.; Roberts and Company Publishers, Colorado, 2009.
McMurry, J., Organic Chemistry, 9th ed.; Cengage Learning, Boston, 2016.
Smith, J. G., Organic chemistry; 6th ed.; McGraw-Hill Education, New York, 2020.
Wade., L. G., Organic Chemistry; 8th ed.; Pearson Education, Inc., United States, 2013.

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