Reacting either of these compounds cis or trans with br 2 should produce 1,2dibromo1,2diphenylethane. Debromination of mesostilbene dibromide by 2tetrahydrofuryl. Double elimination reaction synthesis of diphenylacetylene. Neither the authors, the university of texas at austin, nor cengage learning, inc. What is the melting point of mesostilbene dibromide. Procedure preparation of stilbene dibromide from trans stilbene rinse a clean 250 ml erlenmeyer flask with acetone to remove traces of water.
For more detailed information, consult the material safety data sheet for this compound. Ac147950250 synonyms stilbene dibromide recommended use laboratory chemicals. Diphenylacetylene from stilbene linkedin slideshare. The hazard fields include special hazard alerts air and water reactions, fire hazards, health hazards, a reactivity profile, and details about reactive groups assignments and potentially incompatible absorbents. Classified as a diarylethene, it features a central ethylene moiety with one phenyl group substituents on each end of the carboncarbon double bond. Estilbene, commonly known as transstilbene, is an organic compound represented by the condensed structural formula c 6 h 5 chchc 6 h 5. Debromination of mesostilbene dibromide by 2tetrahydrofuryl hydroperoxide kuniaki iron faculty of science, kwansei gakuin university.
If your answer is no, explain why not, and show what the product would be. Rokkodai, nada, kobeshi 657 japan debromination of meso and dlstilbene dibromides by 2tetrahydrofuryl hydroperoxidethf hpo in thf and its reaction. Ac161040000, ac161040250, ac16104, ac161045000, ac419720000, ac419720250 ac419720250 synonyms. The aim of this experiment is to carry out an addition reaction using transstilbene and bromine reagent to produce 1,2dibromo1,2diphenylethane. Would you obtain the same final product by this experimental procedure if you used cis stilbene instead of trans stilbene. The information given is designed only as a guidance for safe handling, use, processing, storage, transportation, disposal and release and is not to be considered a warranty or quality specification. What is the molecular formula of mesostilbene dibromide. Two pellets of potassium hydroxide were retrieved only after finishing setting up the conical vial with its solution because the pellets decompose rather quickly, so if left out for too long prior to being used, they turn into mushy pods. Dehydrohalogenation of mesostilbene dibromide preparation of diphenylacetylene if you dont have enough mesostilbene dibromide from part 1, you can obtain some from the reagent hood.
Safety data sheet revision date 18jan2018 revision number 3 1. Mesostilbene dibromide contains the elements carbon, hydrogen, and bromine. Mesostilbene dibromide stilbene has a melting point range of 220. The other isomeric product is a racemic mixture often called or a d,l pair. Meso stilbene dibromide has a molecular formula of c14h12br2. My product had a closer melting point to the mesostilbene dibromide than the racemic, proving the bromination was successful.
The aim of this experiment is to carry out an addition reaction using trans stilbene and bromine reagent to produce 1,2dibromo1,2diphenylethane. Oct 26, 2009 diphenylacetylene from stilbene slideshare uses cookies to improve functionality and performance, and to provide you with relevant advertising. Mesostilbene dibromide has a molecular formula of c14h12br2. It doesnt matter which stilbene is used for this reaction, estilbene and zstilbene will both produce 1,2dibromo1,2diphenylethane. Department of chemistry, faculty of science, kobe university. Conclusion this reaction began with the addition of meso. The result is a trans dibromide, as shown in the equation below. Sigmaaldrich 3050 spruce street saint louis mo 63103 usa telephone. Ac147950000, ac147950050, ac147950250, ac14795 synonyms.
Meso compounds, such as 106550, are unique in that there are chiral carbons in the molecule yet they are not optically active. The information provided in this safety data sheet is correct to the best of our knowledge, information and belief at the date of its publication. Generally, chiral molecules are optically active, rotating polarized light. Would you obtain the same final product by this experimental procedure if you used cis stilbene instead of transstilbene. Bromination of cinnamic acid royal society of chemistry. Post your questions about chemistry, whether theyre school related or just out of general interest. If you continue browsing the site, you agree to the use of cookies on this website. Check to be sure the lab jack holding your hot plate is raised a few inches. C while the racemic mixture has a melting point of 110. Weigh approximately 150 mg of the mesostilbene dibromide, prepared in part 1. Diphenylacetylene from stilbene slideshare uses cookies to improve functionality and performance, and to provide you with relevant advertising. Search results for stilbene dibromide at sigmaaldrich. The purpose of this experiment was to synthesize the second intermediate mesostilbene dibromide in the estilbene reaction by bromination.
Section 1 chemical product and company identification product name pyridinium tribromide statement of hazardous nature considered a hazardous substance according to osha 29 cfr 1910. Conclusion this reaction began with the addition of meso stilbene dibromide into a conical vial containing triethylene glycol. The cinnamic acid is soluble in dichloromethane at room temperature and thus before the bromine addition the reaction vessel holds a colourless solution. 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 mesostilbene dibromide along with minor amounts of. Product and company identification product name meso. The meso isomer, which has a mirror plane down its vertical symmetry axis, would be the r,s stereoisomer, because mirroring the r configuration gives you the s configuration. Identification product name 1,2dibromo1,2diphenylethane cat no. Other hazards which do not result in classification. Enantiomers are equal in all their physical properties except for their optical rotation, as they rotate the plane of polarized light by equal amounts in opposite directions. Conclusion this reaction began with the addition of mesostilbene dibromide into a conical vial containing triethylene glycol.
Chemspider id 2034487 2 of 2 defined stereocentres. Benzene, 1,1 1,2dibromo1,2ethanediylbis molecular weight. Draw a newman projection for the stilbene dibromide product. Stir the mixture in a heated sand bath until most of the potassium. Apr 15, 2008 for the best answers, search on this site i dont actually know what stilbene looks like, but i would assume that it has two steriocenters and that the mesoform dd stilbene im guessing is superimposable on its mirror image ll stilbene while dl stilbene is not superimposable on its mirror image ld stilbene so they therefore exist as a pair of enantiomers.
If these are formed it will be as the racemic mixture mp 114115 c. Material safety data sheet 1,2dibromo1,2diphenylethane, 96. If you have enough, however, you should use the material that you prepared. For the best answers, search on this site i dont actually know what stilbene looks like, but i would assume that it has two steriocenters and that the mesoform ddstilbene im guessing is superimposable on its mirror image llstilbene while dlstilbene is not superimposable on its mirror image ldstilbene so they therefore exist as a pair of enantiomers. Material safety data sheet meso1,2dibromo1,2diphenylethane sc228455. Meso stilbene dibromide contains the elements carbon, hydrogen, and bromine.
The stilbene dibromide meso1,2dibromo1,2diphenylethane is generated by reaction of trans stilbene with br 2 generated by pyridinium tribromide. Write a mechanism for the bromination reaction of e stilbene to form mesostilbene dibromide. 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. The stilbene dibromide meso1,2dibromo1,2diphenylethane is generated by reaction of transstilbene with br 2 generated by pyridinium tribromide. Bromination of cinnamic acid supplementary material experimental notes this experiment aims at the preparation of the 2,3dibromo3phenylpropanoic acid from cinnamic acid by bromine addition. Best answer 100% 1 rating previous question next question. It was hypothesized that if the reaction was heated at 120c for five minutes the reaction between estilbene and the pyridium bromide perbromide would occur, and mesostilbene would be created.