This then provides a slower release of bromine into the reaction medium. It was expected that e stilbene after undergoing bromination in a solution of acetic acid would produce crystals of mesostilbene. Feb 15, 2012 organic chemistry i, chem 2700, university of guelph. Into a 50 ml round bottom flask equipped with a magnetic stirbar, add 500 mg e stilbene and10 ml ethanol. Bromination of estilbene lab report 1031 words bartleby. Although the percent yield was low the experiment did produce mesostilbene dibromide. Organic chemistry i, chem 2700, university of guelph. However, bromination of the z isomer results in a racemic mixture of dl stilbene dibromide, while the bromination of an e isomer results in a majority meso stilbene dibromide along with minor amounts of the. Bromination of stilbene in the experiment entitled steam distillation, you demonstrated that eugenol has one or more carboncarbon double bonds by reacting it with bromine, br 2, and observing the discharge of the reddishbrown color of bromine as each drop reacted with the double bond in eugenol. The reagents used are less toxic than other reactant typically used. All reagents were loaded in syringes, but while the hbr, naocl and na 2 so 3 were pumped by chemyx fusion 100 syringe pumps, the cyclododecatriene was pumped by a harvard phd. Materials and methods first, a water bath was prepared and heated to 90100oc on a hot plate. As described in mayo, bromination uses pyridinium tribromide which is.
Practical approach to green chemistry, international journal of pharmacy and. Green source of bromine e 1,2diphenylethene chemical formula. A multistep synthesis incorporating a green bromination of an. Ecofriendly and versatile brominating reagent prepared. The reaction of bromine with e stilbene is a classic reaction performed as an example of an electrophilic addition reaction of alkenes.
Symposium coordinator for the gci electrophilic bromination is a common type of reaction in undergraduate organic laboratories. Check to be sure the lab jack holding your hot plate is raised a few inches. Chem 212 lecture notes summer 2012, diphenylacetylene. Applying green chemistry principles in the electrophilic bromination of indole3acetic acid kyle murphy t he goals of green chemistry are to reduce or eliminate the use of hazardous reagents, prevent the synthesis of toxic products and byproducts, and improve the overall efficiency of chemical reactions. Estilbene, commonly known as trans stilbene, is an organic compound represented by the condensed structural formula c 6 h 5 chchc 6 h 5. Green chemistry modification involves application of a. Hydroxylated derivatives of stilbene stilbenoids are secondary products of heartwood formation in trees that can act as phytoalexins antibiotics produced by plants. The original process for bromination of 1 employed nbromosuccinimide in dichloromethane with benzoyl peroxide as radical initiator. Procedure preparation of diphenylacetylene from stilbene dibromide place approximately 3 g of potassium hydroxide into a 100 ml roundbottom flask and add 30 ml of ethylene glycol and a magnetic stir bar.
Dec 01, 2014 the evolution of a green chemistry laboratory experiment. The bromination of stilbene experiment is green because. Instead of this reaction, the oxidation of hydrobromic acid and hydrogen peroxide. This practical involves the bromination of trans stilbene using a 10% bromine dichloromethane solution. The reaction is stereospecific through an anti addition to the double bond. This experiment is multifaceted and can be used to teach students about protecting groups. Rearrangement of transstilbene oxide with bismuth trifluoromethanesulfonate and other metal triflates. Because of their various photophysical and photochemical properties, stilbene compounds can be used in various applications in materials science such as optical brighteners used in laundry detergent to enhance. Reaction of bromine with 4, 5dimethyl1, 4cyclohexadiene1, 2. Electrophilic aromatic substitution is a fundamental topic taught in the undergraduate organic chemistry curriculum. Bromination of trans stilbene to form 1,2 dibromo 1,2diphenylethane. For the bromination of e stilbene the results were favourable. Bromination of transstilbene with pyridinium tribromide. May 11, 2018 bromine and chlorine readily undergo addition reactions with alkenes.
Place the vial on the stirplate in the aluminum block and stir until the stilbene has dissolved. We describe two new greener alkene bromination reactions that offer enhanced laboratory safety and convey important green chemistry concepts, in addition to illustrating the chemistry. Shende department of chemistry, institute of science, nagpur440 001, india email. Swirl the mixture to start dissolving the stilbene. In this experiment, estilbene is exposed to bromine to produce dibromostilbene. The traditional reaction uses a bromine solution in methylene chloride, which has very high toxcity. Synthesis of stilbene by the wittig and hornerwadsworthemmons reactions important concepts synthetic methods for making double bonds olefins phosphonium salt, ylide, phosphonate ester transition state controls wittig stereochemistry cis ring closure controls wadsworthemmons stereochemistry trans. Clamp over a heating mantle on a stirring hotplate. Electronic supporting information files are available without a subscription to acs web editions. This reaction will lead to the bromination of e stilbene to 1,2 dibromo 1,2 dipheynlethane dibromostilbene. Ghosha received 10th may 2006, accepted 10th july 2006 first published as an advance article on the web 3rd august 2006 doi. The original process for bromination of 1 employed nbromosuccinimide in dichloromethane with benzoyl peroxide as.
This is due to the fact that cis stilbene has different geometries. The bromination of the alkane was calculated and the overall percent yield was 96. Although the percent yield was low the experiment did produce meso stilbene dibromide. E7016 3, scheme 1 is an inhibitor of poly adpribose polymerase currently being investigated clinically as a potential anticancer therapy. Bromination of an alkene is an example of an electrophilic addition reaction. Greener brominations of stilbene article in journal of chemical education 822 february 2005 with 630 reads how we measure reads. Bromination of cinnamic acid royal society of chemistry. It doesnt matter which stilbene is used for this reaction, stilbene and stilbene will both produce 1,2dibromo1,2diphenylethane. The aim of this experiment is to carry out an addition reaction using trans stilbene and bromine reagent to produce 1,2dibromo1,2diphenylethane. To brominate trans stilbene using green principles for the purpose of verifying the mechanism.
New solventfree brominations of 1,3dicarbonyl compounds, phenols, various alkenes including chalcones, azachalcones, 4phenylbut3en2one, methyl cinnamate, styrene and 1,3cyclohexadiene were efficiently achieved by employing sodium bromide and oxone under mechanical milling conditions. Adapted from green organic chemistry, kenneth m doxsee and james e. Classified as a diarylethene, it features a central ethylene moiety with one phenyl group substituents on each end of the carboncarbon double bond. Hence, an addition reaction takes place an 1,2dibromo1,2diphenylethane is formed. Bromination of trans stilbene preparation of meso stilbene dibromide add approximately 180 mg of trans stilbene mw 180 gmol and 2. We did a lab where we used bromination of stilbenes. Pdf a greener bromination of stilbene and qualitative. Ecofriendly and versatile brominating reagent prepared from a liquid bromine precursorsubbarayappa adimurthy,a gadde ramachandraiah,a ashutosh v. Ecofriendly and versatile brominating reagent prepared from. Procedure preparation of stilbene dibromide from trans stilbene rinse a clean 250 ml erlenmeyer flask with acetone to remove traces of water. The alkene, trans stilbene, acts as a nucleophile and the bromine acts as an. We describe two new greener alkene bromination reactions that offer enhanced.
The two alternative reactions, one involving pyridinium tribromide and a second using hydrogen peroxide and hydrobromic acid, are compared to the traditional bromination of stilbene. Bromination of substituted alkenes can produce different stereoisomers based on the geometrt of the alkene. This dense brownishred liquid is a pain in the butt for a few reasons. The name for stilbene 1,2diphenylethylene was derived from the greek word stilbos,whichmeansshining. As most chemicals used in this experiment are toxic harmful, ppe must be used throughout and the experiment should be carried out inside a fume hood. Bromination of ethyl cinnamate important references. Bromination of e chalcones e1,3diarylprop2en1ones supplementary material in this work, which is planned for a 4 hours session, students individually or in groups of two will.
Stir the mixture in a heated sand bath until most of the potassium. Synthesis of stilbene by the wittig and hornerwadsworth. Kinetics and mechanism of the bromination of salicylic acid. In india although green chemistry is being taught in a few colleges and universities, laboratory experiments remained largely the same as being taught fifty years back. The use of green metrics to compare three bromination laboratory procedures demonstrates the effectiveness of an incremental greening process for chemistry curricula. Because of the chemical stability of phenyl moiety of 1,2diphenylethylene, stilbene is not a suitable starting compound for synthesis of stilbene derivatives. It was expected that estilbene after undergoing bromination in a solution of acetic acid would produce crystals of meso stilbene.
As described in mayo, bromination uses pyridinium tribromide which is corrosive, potentially damaging. Adapted from john thompson, lane community college purpose. Greener bromation of stilbene alkene chemical reactions free. The product is the d,l diasteriomer of 1,2dibromo1,2diphenylethane. We describe two new greener alkene bromination reactions that offer. Example procedures for bromination reactions in organic chemistry. Clark, the first director of the rsc green chemistry network, who in 1999, after presenting challenges facing chemists among which greener bromination processes and opportunities offered by a green approach, concluded the drive towards clean technology in the chemical industry and the. Synthesis of 1,2dibromo1,2diphenylethane adapted from green organic chemistry, kenneth m doxsee and james e. Monograph on green chemistry laboratory experiments. The product of the bromination of cis stilbene would be like the racemic mixture, if you substitute phenyls for carboxyls and bromines for hydroxyls. Yet safer, this reaction is not an atom economical reaction. What product is formed from the bromination of cisstilbene. E stilbene, commonly known as transstilbene, is an organic compound represented by the condensed structural formula c 6 h 5 chchc 6 h 5.
Hutchison b12 in situ br anto a 50 ml round bottom flask equipped with a magnetic stirbar, add ou clamp over a heating mantle on a stirring hotplate. Solventfree bromination reactions with sodium bromide and. It utilizes ethanol as a solvent and bromide is generated in situ from the reaction of hydrobromic acid and hydrogen peroxide. The goal of the lab is to identify which stereoisomer predominates in the reaction and to deduce the structure of the intermediate cation. This experiment is multifaceted and can be used to teach students about protecting groups, multistep synthesis, redox. It has an stereochemistry, meaning that the phenyl groups are located on. In these experiments, we rarely use br2 as a bromine source. This experiment is a green bromination of trans stilbene because it reduces the need to use hazardous chemicals. Greener bromation of stilbene free download as pdf file. A multistep synthesis that includes a safer and greener method for the bromination of an aromatic ring than traditional bromination methods is described.
Define this term and why green chemistry is desirable. A key intermediate in the synthesis of e7016 is benzylic bromide 2, which is prepared via bromination of methylxanthine 1. Jun 04, 2019 an e, e,z1,5,9cyclododecatriene solution of 0. Addition of a halogen to an alkene synthesis of stilbene.
The evolution of a green chemistry laboratory experiment. What is the traditional way to brominate across a double. Bromination of e chalcones e 1,3diarylprop2en1ones supplementary material in this work, which is planned for a 4 hours session, students individually or in groups of two will. Pdf this experiment aimed to utilize stilbene to prepare stilbene dibromide by. A part of the product was burned, and the flames were green. E stilbene trans stilbene, which is not sterically hindered, and z stilbene cis stilbene, which is sterically hindered and therefore less stable. A greener bromination of stilbene and qualitative determination of alkene compounds.
Hutchison journal of chemical education 2005 82 2, 306 j. This was not soluble in methanol or acetone and its melting point was 106108 degrees celcius. This process was employed on kilogram scale to deliver an early batch of e7016. A greener bromination of stilbene kenyon college chem 234 organic chemistry lab ii for the background and mechanism of the experiment read mayo, experiment a2b p.
Bromination of cis and trans stilbene organic chemistry. We describe two new greener alkene bromination reactions that offer enhanced laboratory safety and convey important green chemistry concepts, in addition to illustrating the chemistry of alkenes. A multistep synthesis incorporating a green bromination of. Bromination of trans stilbene experiment 9 page 1 of 3 experiment 9. Bromination of estilbene lab report 1031 words 5 pages bromination of estilbene kelly marroquin fall 2017 lab section. Green chemistry is an essential part of chemistry curriculum. The two alternative reactions, one involving pyridinium tribromide and a second using hydrogen peroxide and hydrobromic acid, are compared to the traditional bromination of stilbene through the. Thus teaching of green chemistry in class room and laboratory should go simultaneously. During the first part of the experiment the yield of mesostilbene dibromide was lower than the theoretical yield could be because the reaction did not go fully to completion. The resultant brominated ketones were isolated in yields of 6997% with high selec.
If these are formed it will be as the racemic mixture mp 114115 c. Bromination of an alkene is an addition reaction covered in an. Apr 04, 2019 a greener bromination of stilbene and qualitative determination of alkene compounds. Using the bromination reagents of hydrogen peroxide and hbr is considered green chemistry. Applying green chemistry principles in the electrophilic. A green bromination process for synthesis of a novel drug. Double elimination reaction synthesis of diphenylacetylene. Mar 29, 2006 we did a lab where we used bromination of stilbenes. Due to this process, the bromination of alkenes can be introduced to students through the use of a safe, effective, modern practice.
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