Expanding a Molecular Formula to Constitutional Isomers in Organic Chemistry
Matthew Donahue Matthew Donahue
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 Published On Sep 2, 2024

In this organic chemistry screencast, the molecular formula C6H12 is expanded into constitutional isomers having either one pi bond or one ring. Using the general alkane molecular formula of CnH2n+2, the degrees of unsaturation are calculated. A degree of unsaturation being equivalent to a molecule of hydrogen H2, we find that the C6H12 molecular formula has one degree of unsaturation. Therefore, we can begin to propose isomers that have either one pi bond or one ring. In the logical approach, we start with the longest carbon chain of six atoms with one pi bond to propose alkene isomers. Alternatively, we start with the largest ring of six carbon atoms. Then analyzing the attached hydrogens as methyl, methylene, methine or no attached hydrogens, we classify the total number of carbons. Each carbon is then tested for uniqueness which relates the symmetry of the molecule. The symmetry elements being tested are either a mirror plane or an axis of rotation. We find our initial results will stay the same or change if there is symmetry. Using the same logic, the hydrogen sets are then determined along with their ratios. As we examine higher carbon count molecular formulas, we will see that more and more isomers can be proposed. The uniqueness approach to differentiating them allows us to understand how the actual NMR data will look. Additionally, the nomenclature helps us understand the differences between linear and branched compounds. Furthermore, the shape of the molecule will then impact the physical properties such as melting and boiling points.

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