Modified Birch Reduction for the Introductory Undergraduate Organic Laboratory
Bradley, Lynn M.
Lareau, Nichole M.
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The Birch reduction is a reaction commonly taught in the second-year undergraduate organic curriculum that involves the reduction of an aromatic compound to an alicyclic product using sodium metal and liquid ammonia. The experimental procedure can be challenging for novice chemists and thus has not been widely performed in introductory organic laboratories. An experimental procedure appropriate for introductory organic students is described that utilizes commercially available sodium-impregnated silica gel that is safer and easier to handle. This modified Birch reduction effectively reduces naphthalene to 1,4-dihydronaphthalene while minimizing safety concerns associated with the use of alkali metals and liquid ammonia.
Abourahma, H., Bradley, L., Lareau, N. M., & Reesbeck, M. (2014). Modified Birch Reduction for the Introductory Undergraduate Organic Laboratory. Journal Of Chemical Education, 91(3), 443-445.
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