Wittig Reaction Of Trans-Cinnamaldehyde Lab Report

Improved Essays
Maci Mullins
CHEM2130-001
12/8/2017

A Wittig Reaction of trans-Cinnamaldehyde

Statement of Question: What is the stereochemistry in the Wittig product, and why is it formed?

Hypothesis: There were two possible stereochemical outcomes for this experiment, either cis, (E,Z), or trans, (E,E). The cis product, (E,Z), would form if the double bond and phenyl group added to the same side. The trans product, E,E), would form if the double bond and phenyl group were to add to the opposite sides. The product of desire for the Wittig reaction is the trans, (E,E), isomer. Since the trans isomer of cinnamaldehyde was used in the experiment, the addition of one of the two double bonds formed in the major product was expected to be trans (E). The purpose
…show more content…
The Wittig reaction consists of a nucleophilic attack from a negatively charged carbon of the phosphorus ylide on to the carbonyl group carbon. Elimination then occurs to form the carbon to carbon double bond with the assistance of the Ph₃P=O reagent. After elimination is completed, the Ph₃P group and the oxygen of the carbonyl group are no longer present.
In this experiment, the phosphonium salt used was benzyltriphenylphosphonium chloride, which was provided by the instructor. During synthesis of the phosphonium salt, the ylide was formed in the presence of the phenyl group. The phenyl group provides stabilization. The cinnamaldehyde then reacts with the ylide to form a product of 1,4-diphenyl-1,3-butadiene. The ylide-forming reaction occurs in a set of two phases. 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
…show more content…
This value is extremely close to that of the literature value for the trans product, (E,E)-1,4-diphenyl-1,3-butadiene, which is 153°C compared to that of the cis product, (E,Z)-1,4-diphenyl-1,36-butadiene which is 88°C. With just that small amount of data, I was rather sure that I knew what my product was before doing any further analysis. An infrared spectrum was recorded as well and compared to that of the (E,E)-1,4-diphenyl-1,3-butadiene since the melting points were so close. Although I was unable to find an infrared spectrum for that of the cis, (E,Z)-1,4-diphenyl-1,3-butadiene, I was certain of my product after observing the IR of the trans product. There were multiple identical peaks from both my own recorded infrared spectrum and the researched infrared spectrum from the SDBS website (see attached). There were peaks shown to represent aromatic carbon to hydrogen bonds at 618cmˉˡ on both IR spectrums. Peaks were also shown at 3015cmˉˡ on my products recorded IR spectrum and 3016cmˉˡ on the SDBS IR spectrum that represented the carbon to hydrogen bond stretching. There were many other identical peaks which can be observed on the attached infrared spectrums that provide assurance of my formed product as

Related Documents

  • Improved Essays

    The goal of this lab was to conduct the reaction of 2-methyl-2-butanol with HCl to form 2-chloro-2-methylbutane, and to understand Sn1 and Sn2 reactions, in terms of how they are different and why one is more likely to happen over the other. The OH group in 2-methl-2-butanol is attached to a tertiary Carbon, meaning the reaction should occur via Sn1, a two-step reaction, and Cl should replace the OH group, to form a tertiary halide. HCl was added to 2-methyl-2-butanol and then several extractions were done to purify the product. The percent recovery was calculated to be 77.5% and the IR experimental chart highly resembled the IR chart of 2-methyl-2-butanol; these results indicate that few errors occurred in the lab and that the reaction occurred…

    • 995 Words
    • 4 Pages
    Improved Essays
  • Improved Essays

    Alkaline phosphatase catalyzes the hydrolysis and transphosphorylation of phosphomonoesters (1). A kinetic reaction scheme of AP is presented in Figure 2. Figure 2: Kinetic reaction scheme of alkaline phosphatase (11). Under the hydrolysis reaction, free phosphate and an alcohol molecule are released from the active site. The rate-determining step of this reaction is pH dependent.…

    • 2173 Words
    • 9 Pages
    Improved Essays
  • Improved Essays

    Tri-O-acetyluridine (S.1) reacts with MSNT to produce the triazolo derivative S.2 (Figure 2.1.2; Reese and Ubasawa, 1980). During deprotection with ammonium hydroxide, S.2 gives cytidine (S.3). Interestingly, during deprotection with either the tetramethylguanidinium…

    • 1630 Words
    • 7 Pages
    Improved Essays
  • Great Essays

    The experiment made use of two reactions in synthesizing 1-phenylazo-2-naphtol, also known as Sudan-1. The first is the diazotization reaction in which a diazonium salt is formed from the conversion of primary aromatic amines, such as aniline, to compounds with the nitroso functional group using a nitrous acid, such as HNO2. The diazonium salt was then used as an electrophile in a coupling reaction with an aromatic compound, β-naphthol. Recrystallization was conducted and yielded 0.18 g of a red-orange compound. The percent yield was determined to be 33.33%, based on the theoretical yield of 0.54g.…

    • 1448 Words
    • 6 Pages
    Great Essays
  • Decent Essays

    To form ethyl Alcohol, pyruvate needs to give off CO2, from this acetaldehyde is formed. Like in lactate, the substrate NADH + H+ is put in to produce NAD+ This reduction is what produces ethyl…

    • 846 Words
    • 4 Pages
    Decent Essays
  • Improved Essays

    Wittig Reaction Lab Report

    • 1084 Words
    • 4 Pages

    During synthesize of the product, the appearance of the reaction mixture changed. The main solution containing dicholormethane, benzyltriphenylphosphorium and benzaldehyde was cloudy and white. This solution changed colors when the sodium hydroxide solution was added. After only a small amount of sodium hydroxide solution was added, the reaction solution became…

    • 1084 Words
    • 4 Pages
    Improved Essays
  • Improved Essays

    Paracetamol Lab Report

    • 651 Words
    • 3 Pages

    Paracetamol, or Acetaminophen is created by the synthesis and preparation of an amide. It is made when the amine group of 4-aminophenol is acetylated by acetic anhydride to produce paracetamol and the by-product of the reaction, acetic acid. Paracetamol is contains three functional groups; A hydroxyl group (OH), an amide group (HN-CO-R) and an aromatic group (benzene ring).…

    • 651 Words
    • 3 Pages
    Improved Essays
  • Decent Essays

    Stereochemistry 5. Introduction In this experiment, stereochemistry was explored by the isomerization of dimethyl maleate and the analysis of carvones. The isomerization was accomplished with the use of bromine, which broke the double bond to allow bond rotation. Free bond rotation allowed molecules to shift into the trans state before the double bond was reformed to create dimethyl fumarate. Weight and melting point of the crystals formed were taken for further analysis.…

    • 929 Words
    • 4 Pages
    Decent Essays
  • Improved Essays

    Isobutylene Research Paper

    • 1817 Words
    • 8 Pages

    The purpose of this stage is mixing the generated Isobutylene that comes from the Oleflex unit with the excess amount of methanol manufactured by QAFAC to produce MTBE. Two isobutylene spheres (V 3101, V 3102) are designed to store 2,400 m3 other than storing requirements. These spheres can receive isobutylene after shutdown in the downstream and they are continuously charge and receive Isobutylene in initial startup and normal shutdown. The feed passes through highly acidic ion exchange (V 2302), low temperature and relatively high pressure, these conditions are required to mix Isobutylene with methanol to produce MTBE. MX 2301 is the Mixer in this stage of the process that mixes isobutylene that comes from (V 3101, V 3102) with Methanol from Methanol drum (V 2303).…

    • 1817 Words
    • 8 Pages
    Improved Essays
  • Improved Essays

    In the oxidation reaction, the alcohol functional group of benzoin was oxidized to form the carbonyl functional group of benzil, while the nitric acid was reduced into a mixture of nitrogen oxides that formed toxic brown fumes. The final step was the preparation of tetracyclone from the aldol condensation reaction of…

    • 1200 Words
    • 5 Pages
    Improved Essays