CHEM 324 - Experiment 43.docx - Experiment 43 Effect of Reaction Conditions on the Condensation of Furfural with Cyclopentanone Hang Tran 40044938 CHEM

CHEM 324 - Experiment 43.docx - Experiment 43 Effect of...

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Experiment 43Effect of Reaction Conditions on the Condensation of Furfural withCyclopentanoneHang Tran40044938 CHEM 324 – Organic Chemistry IIIConcordia UniversityLab Section: Thursday AfternoonDate Submitted: 28/11/2019
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IntroductionThe purpose of this experiment is study condensation reactions between furfural and cyclopentanone under different conditions. Product A will be synthesized without the use of a phase transfer catalyst (PTC) while Product B will have a PTC present. The resulting two products will be analyzed and contrasted. The type of condensation reaction performed is known as the Claisen-Schmidt reaction.[1]This reaction occurs between an aromatic aldehyde and an aliphatic aldehyde or ketone in the presence of an acid or a base to yield an ,-unsaturated ketone.[2[In this experiment, the reaction will be occurring under basic conditions using NaOH. The sodium hydroxide will deprotonate the most acidic α-hydrogen to form an enolate. The enolate is a soft nucleophile that will then attack the carbonyl carbon of the electrophilic aromatic aldehyde to form a β-hydroxy carbonyl compound which then undergoes a dehydration reaction through an E1cb mechanism into an ,-unsaturated carbonyl.[3]An important technique used in this experiment is that of column chromatography to separate Product A from the crude mixture. This technique involves using a stationary phase of
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silica and a mobile phase of hexanes. The column is first packed with cotton and then a layer of sand to create a flat layer and also prevents any solid from entering the final solution.[1]Then the adsorbent, silica, is added in a slurry, containing the eluant hexanes, to the column. To isolate forthe desired product, the entire crude product is added to the top of the column and allowed to elute through the stationary phase with the help of the flowing mobile phase. Additionally, as all of the crude mixture has eluted into the stationary phase, a layer of sand will be added over the column to ensure that the adsorbent layer is not disrupted while more eluent is added. The separation of the crude mixture in the column depends on the interactions of the mixture’s components with the stationary phase and the mobile phase. The interactions between adsorbent and crude mixture depends on polarity and structural features of the mixture’s components.[1]Thestronger the interaction with the stationary phase, the longer the component will stay in the column. Thus, the components will elute based on their structures and collected accordingly for the desired product. Experimental Data1.Product AApproximately 4mL of cyclopentanone was usedWhen cyclopentanone, ether, and sodium hydroxide were mixed, a yellowish solution formedWhen furfural was added, the solution became a dark yellow/amber solutionWhen washing with diethyl ether, the organic layer was clear and yellow, the aqueous layer was dark brownWhen washing with NaCl, the organic layer was clear and yellow, the aqueous
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