Orgo Post Lab 10

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Running head: DIELS-ALDER REACTION Diels- Alder Reaction: Synthesis of 9,10 – dihydroanthroceno-9,10-edo- α, β-succinic anhydride Anjenelle Fernandez, Steve Smith University of South Florida CHM 2211L: Organic Chemistry II Lab
DIELS-ALDER REACTION 2 Synthesis of a Biodiesel and a Soap Esterification is the term that refers to the process of forming an ester (Clark, 2023). A specific form of esterification is transesterification which refers to the process of obtaining a carboxylic acid ester specifically from a different carboxylic acid ester (Farmer & Gunawardena, 2023). A common way that this occurs is through the utilization of an acid catalyst during a reaction between an ester and an alcohol. Saponification is the formation of soap which occurs through a reaction in which an ester in a water and a base forms a carboxylic acid and an alcohol (Farmer, 2023). However, due to the presence of the strong base, a carboxylic ion is formed in place of the carboxylic acid. An example of transesterification is the formation of biodiesels from triglycerides, for example an animal fat. This occurs the presence of an acid and uses an excess of the alcohol to drive the reaction in the forward direction. One example of saponification is the formation of soap from coconut oil. This reaction occurs in basic conditions and is irreversible.
DIELS-ALDER REACTION 3 Figure 1: Detailed mechanism for the preparation of biodiesel Figure 2: Mechanism for preparation of soap
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+allow to separate for 20-30 minutes + see 2 layers DIELS-ALDER REACTION 4 Figure 3: Potential unwanted side reaction for preparation of biodiesel Figure 4: Potential unwanted side reaction for preparation of soap Experiment Procedures Part A: Preparation of a Biodiesel ] Conical Flask (250 mL) + Stir bar + 300 mg KOH + 8.5 mL methanol + cover flask with parafilm + stir until dissolved + “heated” 32 mL vegetable oil + cover with parafilm + stir at 60 ° C for one hour Separatory Funnel Bottom layer (glycerol) Top layer (biodiesel)
DIELS-ALDER REACTION 5 Biodiesel Part B: Preparation of a Soap Chemicals Top layer (biodiesel) + take 3 mL of biodiesel + do 27/3 MeOH test + pipet out 3mL top layer + pour into measuring cylinder with 27 mL of MeOH + mix + if homogeneous then positive + once identity is confirmed + drain the remaining layer + weigh + calculate % yield Confirms biodiesel 250 mL Beaker + large stir bar + 50 g coconut oil + heat at 100°C + 30% NaOH solution Basic Solution +heat and stir at 90-100°C for one hour until too viscous to stir + transfer molten soap to watch glass let cool + shape and compress the semi-solid soap into a bar +compare cooling soap and let dry for two weeks + coconut soap must be superfatted with coconut oil to avid over drying of skin Graduated Cylinder +add small piece of soap + 5mL of water, shake +foaming? + test pH with litmus paper + CaCl 2 to dry water + foaming diminished? Triacyclglycerol Triaglyceride
DIELS-ALDER REACTION 6 Results Glycerol Formula: C 3 H 8 O 3 Molar mass: 92.09 g/mol Melting point: 18 °C Boiling point: 290 °C IUPAC: propane-1,2,3-triol Hazards: Flammable Can irritate skin and eyes
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DIELS-ALDER REACTION 7 Mass of biodiesel: Color: clear with slight yellow tint Appearance: thick liquid Mass of Soap: 69.2 Odor: coconut Appearance: white, solid, opaque Discussion The overall reaction to prepare tge biodiesel accomplished the original goal and from the green chemistry perspective it is an efficient and low cost way to form a biodiesel in a way that is good for then environment in that it does not produce any harmful biproducts and is from a renewable source, a vegetable fat. In the preparation of soap, this reaction is important because it efficiently forms a soap with no harmful biproduct and produces little waste. This is important as it allows for the formation of soaps and biodiesels in large volumes in a way that is good for the environment and can replaces other methods that are harmful to the environment. Conclusion In conclusion, the data collected by the experiment does connect to theory as the aim of synthesizing the biodiesel and soap was accomplished. The data reveals that one can form a soap and a biodiesel from a vegetable or animal fat. The techniques of this experiment can be applied to form other biodiesels from different forms of animal or vegetable fats than those used in this experiment.
DIELS-ALDER REACTION 8 References Clark, J. (2023, January 23). Making esters from alcohols . Chemistry LibreTexts. Retrieved April 20, 2023, from https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Org anic_Chemistry)/Esters/Synthesis_of_Esters/Making_Esters_From_Alcohols Farmer, S. (2023, January 23). Saponification . Chemistry LibreTexts. Retrieved April 20, 2023, from https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Org anic_Chemistry)/Esters/Reactivity_of_Esters/Saponification Farmer, S., & Gunawardena, G. (2023, January 23). Transesterification . Chemistry LibreTexts. Retrieved April 20, 2023, from https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Org anic_Chemistry)/Esters/Reactivity_of_Esters/Transesterification Weldegirma,S. (2023).  Experimental organic chemistry laboratory manual: CHM 22110L and CHM2211L . University of South Florida.