Oxidation of 2-Ethyl-1,3-Hexanediol with Calcium Hypochlorite, Papers of Organic Chemistry

Download Oxidation of 2-Ethyl-1,3-Hexanediol with Calcium Hypochlorite and more Papers Organic Chemistry in PDF only on Docsity! Mitchell 1 Oxidation of 2-Ethyl-1,3-Hexanediol with Calcium Hypochlorite Analysis Kelli Mitchell Augusta University Chem 3412L Dr. Miao March 20, 2023 Introduction The purpose of this experiment is to understand the reaction between 2-ethyl-1,3-hexanediol and calcium hypochlorite. Since 2-ethyl-1,3-hexanediol includes a secondary and primary hydroxyl groups, depending on location one alcohol might be more reactive than the other OH group. This might lead to the possibility of oxidizing one alcohol group without performing that task to the other OH group. In order to oxidize an alcohol and not the other hydroxyl group, calcium hypochlorite will be used as the oxidant. The understanding of the mechanism behind this investigation will help prove the products that were produced at the end of the experiment. Observations, yield data, and the interpreting of IR spectra graph will help identify what product was created in this lab. Mitchell 2 Line Reaction Possible Products Experimental Section In a small, dry Erlenmeyer flask, measure out 0.526g of 2-ethyl-1,3-hexanediol while the flask is on the scale. Place a stir bar and add about 3.0 mL of glacial acetic acid. Now, place the mixture in an ice bath and slowly add 3.0 mL of aqueous calcium hypochlorite. It is important to not let the reaction get too hot, but also keep in mind that acetic acid might freeze in the ice bath, so have the calcium hypochlorite ready as the mixture begins to cool. Once the calcium hypochlorite is added, remove the flask containing the mixture from the ice bath and stir at room Mitchell 5 form at the end of this experiment, only one came close to the IR spectra. According to the IR spectrum graph, the broad peak at 3357 demonstrates an O-H group. The peaks between𝑐𝑚−1 2959 - 2875 signify a C-H bond of an aldehyde group. Another peak that can be𝑐𝑚−1 𝑐𝑚−1 looked at is peak 1704 . It is a short peak, but can explain the C=O group. From these𝑐𝑚−1 observations, the product that was created in this investigation was 2-Ethyl-3-hydroxyhexanal. When looking at reactivity on primary and secondary alcohols between calcium hypochlorite being the oxidizing agent in this lab, the primary alcohol can be concluded that it is more reactive than the secondary alcohol. The bulkiness around the secondary alcohol makes it harder to react with, therefore not being as reactive on the primary alcohol. Since calcium hypochlorite is considered a weak oxidizing agent, Ca can really only oxidize the primary alcohol due(𝑂𝐶𝑙) 2 to reactivity versus not reacting secondary alcohol. If a different oxidizing agent was used within this experiment like the product would be completely different and here’s why.𝑁𝑎 2 𝐶𝑟 2 𝑂 7 Potassium permanganate will completely oxidize all alcohol groups to the corresponding groups that can be oxidized. If this agent was used, the product formed out of this experiment would look like Figure 1. Figure 1: Oxidized Product if was used𝑁𝑎 2 𝐶𝑟 2 𝑂 7 Mitchell 6 IR spectra of 2-Ethyl-3-Hydroxyhexanal Conclusion In this experiment, 2-ethyl-1,3-hexanediol and calcium hypochlorite were reacted together to produce a product. Multiple products from this experiment could form and it is up to key observations to pinpoint to an accurate answer for the product obtained in the lab. The product created in this experiment is 2-Ethyl-3-hydroxyhexanal and understanding the importance of Mitchell 7 reactivity between secondary and primary alcohols help establish why one hydroxyl group oxidized and the other did not change. The use of IR spectrum, calculating theoretical yield and percent yield, can help conclude the product formed in this experiment.