Ethyl Cinnamate Synthesis

Great Essays
Experiment 5 Synthesis and NMR Spectroscopy of ethyl cinnamate
Introduction:
Wittig reactions involve the stereoselective synthesis of olefins from phosphonium ylides and aldehydes or ketones, where the carbonyl bond is converted to an alkene double bond.1 The variety of suitable reagents and the relatively mild experimental conditions facilitate their industrial applications, such as the synthesis of epoxides, esters, carotenoids and vitamin A.2,3 Specifically, the ester ethyl cinnamate is used as a flavouring agent and in perfumes.
The diastereomers of the alkene are distinguished through Proton Nuclear Magnetic Resonance (1H NMR) spectroscopy, where the coupling constants of alkenyl protons are different for (E) and (Z) isomers.4 It is often
…show more content…
A sample of this reaction mixture (100 μL) was added to dichloromethane (0.5 mL). Potassium carbonate (5 mL, 5 mmol) was added to the rest of the reaction mixture which was then placed in the sonication bath. A sample of the dichloromethane layer (100 μL) was extracted out every 8 minutes and added to dichloromethane (0.5 mL) until the 32nd minute. All the samples, along with benzaldehyde and ethyl cinnamate solutions were analysed by TLC with the eluent prepared from hexane (8 mL) and dichloromethane (2 mL), and then stained with …show more content…
The IR spectrum of this product was acquired as shown in figure 2, where the peaks were present at 3061.55 "c" "m" ^"-1" , 1707.53 "c" "m" ^"-1" , 1637.67 "c" "m" ^"-1" , 1173.41 "c" "m" ^"-1" and 734.73 "c" "m" ^"-1" . Respectively, these indicated the presence of C-H bonds on the aromatic ring and the ethyl group, the carbonyl group, the alkene bond stretches, the C-O bond of the ester and the alkene bond bends. Subsequently, the ethyl cinnamate was identified by the characteristic alkene bond and the ester

Related Documents

  • Improved Essays

    Wittig Reaction Lab Report

    • 1084 Words
    • 4 Pages

    The singlets in RM-09-1 were found at 7.11 ppm and 6.59 ppm. The reported values, found on SDBS, for the chemical shifts of these singlets were 6.57 ppm for (Z)-stilbene and 7.15 ppm for (E)-stilbene. These peaks also determined the ratio of isomers for the second and third fractions as well. In the spectra RM-09-2, the ratio was determined to be 4:3. The singlets on this spectrum were found at 7.11 ppm and 6.59 ppm as well.…

    • 1084 Words
    • 4 Pages
    Improved Essays
  • Great Essays

    In the Acid-Catalyzed Hydration of norbornene, water and sulfuric acid were added to the C=C double bond to form norborneol. Sulfuric acid acted as a catalyst, where it was not consumed in the reaction and helped to propel the reaction forward, as it was vital in forming hydronium ion and breaking the double bond. Both the products endo-norborneol and exo-norborneol were synthesized; however regioselectivity and stereoselectivity played a role as to which product was more preferred and whether the equatorial or axial orientation of the hydroxy group was favored. The setup of the Cold-Finger, and the ability of norborneol to sublime readily allowed for the purification of the crude product to obtain the diastereomeric products exo- and endo-norborneol.…

    • 1629 Words
    • 7 Pages
    Great Essays
  • Superior Essays

    Introduction: The purpose of this experiment is to determine the product that is produced from sodium hypochlorite oxidizing 2-ethyl-1,3-hexanediol and this experiment is to also determine if sodium hypochlorite is a selective oxidizing agent. This reaction is an oxidation reaction. The reaction involves the removal hydrogens and sometimes the addition of oxygen. 2-ethyl-1,3-hexanediol will undergo an oxidation reaction to produce an unknown product (Scheme 1). (1) Scheme 1. 2-ethyl-1,3-hexanediol undergoes a reaction with sodium hypochlorite and glacial acetic acid to produce an unknown product.…

    • 1586 Words
    • 7 Pages
    Superior Essays
  • Improved Essays

    Unknown Compounds

    • 816 Words
    • 4 Pages

    Given an unknown compound in container 3, solubility tests, cation tests, anion tests, and conductivity tests can be used to determine the various properties of the unknown to then make a positive identification of the unknown. These results will not only show chemical and physical properties but also what the unknown compound might react with to form other compounds. After performing the four anion tests, a positive identification was able to be made showing that the unknown compound contained a chloride ion since a white precipitate was formed from the reaction (Table 1). The sulfate, nitrate, and carbonate tests all yielded negative results when no precipitate was formed. The reaction of the chloride anion is as follows: Cl-…

    • 816 Words
    • 4 Pages
    Improved Essays
  • Improved Essays

    Dichloromethane was used as the organic layer of the reaction, which was later evaporated. The benzyltriphenylphosphonium chloride helps to transfer the ylide from the aqueous layer to organic layer. After this occurrence, the ylide then reacted with the cinnamaldehyde. A majority of the major product stayed in the organic layer, but some was recovered from the aqueous layer. After trituration and recrystallization, the product formed was weighed (~0.025g) and a melting point and IR spectrum was recorded for further…

    • 858 Words
    • 4 Pages
    Improved Essays
  • Improved Essays

    Goals The goal of the lab was to investigate the properties and structure of an unidentified compound that was discovered in a local landfill. The group was called in to help determine the chemical and physical properties of the compound so we can let the people of the town know so it can be taken care of properly with or without further precautions to be taken. Another goal of this project was to devise the synthesis of the unknown compound. Experimental Design In order to determine the correct identity of our unknown compound, we first started with a couple preliminary tests, which include physical state and smell.…

    • 757 Words
    • 4 Pages
    Improved Essays
  • Improved Essays

    IR- and H-NMR-spectrum were taken. The Iodide is in the para position (also known as 5-iodosalicylamide), this is confirmed by the IR and the…

    • 960 Words
    • 4 Pages
    Improved Essays
  • Improved Essays

    Dehydration is known as the process of removing water. During chemical dehydration covalent sigma bonds are broken into a hydroxyl group and a covalent sigma bond is broken to a hydrogen on an adjacent atom. A covalent pi bond forms between the two atoms on which the OH and H are bound and therefore chemical dehydration forms a new water molecule along with a new double bond. In this experiment 2-methycyclohexanol will react with phosphoric acid, the phosphoric acid will act as a catalyze.…

    • 483 Words
    • 2 Pages
    Improved Essays
  • Decent Essays

    INTRODUCTION The purpose of this experiment was to demonstrate the stereochemistry of the electrophilic addition using (E)-Stilbene, a trans-isomer of ethylene. Bromine was added and reacted with (E)-Stilbene to form an alkene. A product was made with both a meso-stilbene dibromide and a d/l-stilbene dibromide, which is trans-stilbene dibromide. DISCUSSION AND CONCLUSION For the reaction to form these two different compounds with the same starting reactants, the double bond of (E)-Stilbene has to attack one bromide.…

    • 442 Words
    • 2 Pages
    Decent Essays
  • Decent Essays

    This experiment has successfully synthesize an alkene product name Trans-9-(2-phenylethenyl)anthracene using the Wittig method. This involved creating an Ylide by reacting a base with benzyltriphenylposphonium. The Ylide reacts with an aldehyde reagent to yield the desired alkene product. The information in this lab can be used during the manufacturing of drugs by the pharmaceutical industry.…

    • 94 Words
    • 1 Pages
    Decent Essays
  • Improved Essays

    The key piece of data was the comparison between the melting point ranges of the unknown enantiomer and the known product of (2S, 3R)-2,3,-dibromo-3-phenylpropanoic acid. The mechanism which produced this product was the anti addition mechanism for the bromination of trans-cinnamic acid because the other mechanism would have produced a product with a significantly lower melting point. In order to determine the percent recovery, a mass of the completely dried crude product should have been taken. Differentiating between the (2R, 3S and 2S, 3R) enantiomer to determine the exact product could have been performed to observe the optical rotation using a…

    • 976 Words
    • 4 Pages
    Improved Essays
  • Improved Essays

    The purpose of this experiment was to use aldol condensation methods to synthesize colored cyclopentadienone and then UV/VIS spectrophotometry to characterize the dienone structure synthesized. The information gathered from the UV/VIS analysis was then compared to a computer model of the desired product to analyze the optimal 3D structure of the dienone. The base catalyzed condensation reaction was used to form the product for analysis, followed by vacuum filtration to recover the product. Both a melting point analysis and a UV/VIS analysis were used to analyze the composition of the obtained product. Finally, the computer model was examined to learn about the optimal angles and strain within the molecule.…

    • 1096 Words
    • 5 Pages
    Improved Essays
  • Decent Essays

    Abstract: Dibenzalacetone was synthesized with 5.772 g of pure product recovered. It was equivalent to 82% total yield and 65.99% recover from the crude product. Cis-trans and trans-trans isomers of dibenzalacetone were confirmed to be in the product by Infrared spectrum and melting point analysis. Although 2 isomers were existed, trans-trans was confirmed to be the major product due to its stability. Statement and purpose…

    • 181 Words
    • 1 Pages
    Decent Essays
  • Improved Essays

    Cinnamaldehyde Lab Report

    • 458 Words
    • 2 Pages

    The cinnamaldehyde and water distillate was obtained from the previous lab session and was observed for changes. The oil was on the bottom of the flask. The distillate turned clear when initially it was white. The distillate still had a cinnamon smell. The cinnamaldehyde was now to be extracted from water using an organic solvent.…

    • 458 Words
    • 2 Pages
    Improved Essays
  • Improved Essays

    The melting point of the product at this step was 145.9-147.1°C, which is slightly below the 150 ° C melting point of pure N-acetyl-p-toluidine but much higher than the 43°C melting point of the beginning p-toluidine. The slightly lower melting point could be caused by impurities in the sample. Along with melting point results, the IR spectrum shows a single N–H stretch peak at 1659.31 cm-1 showing the addition of a C=O and shows a peak at 3287.55 cm-1 which suggests an amide while the IR of sample 1 shows N–H stretches at 3416.53 cm-1 and 3334.84 cm-1 which suggests an amine. The 1H NMR shows the addition of an amide by having a peak of three hydrogens at 2.305 ppm that did not exist on the NMR of the…

    • 878 Words
    • 4 Pages
    Improved Essays