Category
Poster - Applied
Description
Bromination reactions are an important type of reaction in Organic Chemistry, with a wide range of industrial applications. Several different types of bromination reactions exist, and a wide variety are used in chemistry education. At Liberty University, they are the first organic reactions discussed in the first semester of Organic Chemistry. Therefore, the laboratory component of the topic should be easy to perform and understand for the students. Currently, the laboratory experiment consists of a radical bromination of a cinnamic acid derivative. NBS is the brominating agent; it is preferrable to bromine, which is highly volatile and acutely toxic. AIBN acts as a radical initiator. The process is simple: the reagents are weighed out, added to a flask, and stirred and heated in an organic solvent for forty-five minutes. The product is then precipitated in ice-cold water and isolated by vacuum filtration. The entire experiment can be completed in a three hour lab period. However, the final product is an uninteresting white powder almost identical to the starting material, and a decarboxylation side-reaction reduces yields unnecessarily. The purpose of the present research is to find a compound that can be brominated under the same conditions with less side-products and result in a more visibly distinct product. To find a suitable compound, numerous bromination reactions will be performed under the same constraints and conditions of the existing lab to determine which produces the product and procedure most suited for illustrating the topic to students. Two compounds are currently being tested; the results of these experiments will inform compound selection for future research.
Optimizing a Lab-Friendly Radical Bromination Reaction
Poster - Applied
Bromination reactions are an important type of reaction in Organic Chemistry, with a wide range of industrial applications. Several different types of bromination reactions exist, and a wide variety are used in chemistry education. At Liberty University, they are the first organic reactions discussed in the first semester of Organic Chemistry. Therefore, the laboratory component of the topic should be easy to perform and understand for the students. Currently, the laboratory experiment consists of a radical bromination of a cinnamic acid derivative. NBS is the brominating agent; it is preferrable to bromine, which is highly volatile and acutely toxic. AIBN acts as a radical initiator. The process is simple: the reagents are weighed out, added to a flask, and stirred and heated in an organic solvent for forty-five minutes. The product is then precipitated in ice-cold water and isolated by vacuum filtration. The entire experiment can be completed in a three hour lab period. However, the final product is an uninteresting white powder almost identical to the starting material, and a decarboxylation side-reaction reduces yields unnecessarily. The purpose of the present research is to find a compound that can be brominated under the same conditions with less side-products and result in a more visibly distinct product. To find a suitable compound, numerous bromination reactions will be performed under the same constraints and conditions of the existing lab to determine which produces the product and procedure most suited for illustrating the topic to students. Two compounds are currently being tested; the results of these experiments will inform compound selection for future research.
Comments
Undergraduate