Old Dominion University ORGANIC 214 Alkene Addition Submitted by: Alkene addition: Bromination of (E) Stilbene Introduction: In this lab we used the greener approach‚ which involves the addition of bromine across a double bond. When bromine reacts with E-stilbene (trans-1‚2-diphenylethene)‚ two new chiral carbons are created from the sp2 carbons‚ therefore 3 different dibrominated stereoisomers are possible: meso-(1R‚2S)‚ or the raceminc mixture-(1R‚2R) or (1S‚2S)-dibromo-1‚2-diphenylethane
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Lab 1: Alkene Addition: Bromination of (E)-stilbene I. Introduction: 1. The purpose of the experiment was to perform an electrophilic addition reaction by using pyridinium tribromide to brominate (E)-stilbene and to identify whether it formed the meso- or racemic product through melting point analysis. 2. This is the mechanism for the bromination of (E)-stilbene. However‚ this is the mechanism for Br2 and in class we us Pyridinium Tribromide instead due to the difficulties associated
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Bromination of Trans-Cinnamic Acid Christopher B. Martin CHEM 3411 1 Mechanism of Bromine Addition to Alkenes Understanding the chemical mechanism (order of bonds broken and made as well as intermediates formed) has a great value in chemical synthesis. The chemical mechanism of a reaction will influence the rate of the reaction‚ the stereochemistry of the product(s)‚ and the extent of possible undesired side reactions. Organic reaction mechanisms investigate the path towards a desired product
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experiment was to perform an electrophilic addition reaction by the bromination of cinnamic acid. The product of this reaction is 3-Phenyl-2‚3-dibromo propionic acid‚ which is purified by recrystallization. Cinnamic acid (3-phenylprop-2-enoic acid) is an unsaturated carboxylic acid. The electron rich π cloud (see Figure 1) in the double bond of this structure is nucleophilic and can be considered a Lewis base. It can therefore be saturated by the addition of a halogen to the double bond. Both of the
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Preparation u Alcohols when heated in presence of H2SO4‚ H3PO4‚ P2O5‚ Al2O3 or BF3 undergo loss of water molecule with the formation of alkene. Conc. H2SO4 180oC H3PO4/P2O5 200oC Al2O3/BF3 350oC CH3-CH=CH2 + H2O CH3-CH2-CH2-OH CH3-CH=CH2 + H2O CH3-CH=CH2 + H2O u u Mechanism: In the first step OH group of the alcohol is protonated in a fast reversible reaction. Unlike OH group‚ protonated OH group is a good leaving group. Step 1: CH3 CH3-C-CH3 + H+ HO CH3 CH3-C-CH3 H2O+
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Greener Brominations Abstract In this experiment‚ trans-stilbene was brominated and debrominated with the use of three methods: bromination with pyridinium tribromide‚ bromination with hydrogen peroxide and hydrobromic acid‚ and debromination with zinc. The yields of parts A‚ B‚ and C are as follows: 68.6 %‚ 54.6 %‚ and 55.9 %. Introduction In the chemical process of bromination‚ an alkene is halogenated with bromine. Solvents that are typically used include methylene chloride and carbon
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Bromination of Acetanilide Objective: The objective of this experiment was to use melting point and NMR to determine which of two isomers‚ ortho or para‚ would most likely form after brominating Acetanilide through electrophilic aromatic substitution. Procedure/Observations: 1. Weigh out ~280 mg of acetanilide in a 10 mL r.b. flask with a stir bar. 2. Then‚ add 2.0 mL of glacial acetic acid using a calibrated Pasteur pipet. 3. Stir the mixture until all of the acetanilide has dissolved
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to the carbon chain than alkanes. Are alkenes with double bonds. Are alkynes with triple bonds. 1 Structure of Alkenes Alkenes (and alkynes) are unsaturated hydrocarbons Alkenes have one or more double bonds The two bonds in a double bond are different: - one bond is a sigma () bond; these are cylindrical in shape and are very strong - the other is a pi (π) bond; these involve sideways overlap of p-orbitals and are weaker than bonds Alkenes are flat and have a trigonal planar shape
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Bromination of Acetanilide Introduction: Bromination of acetanilide to 4-bromoaniline was studied in this experiment. One of the most important mechanism with the reaction of aromatic compounds is the electrophilic aromatic substitution reactions(wade‚2013). The electrophilic aromatic substitution enable scientists to make substituted aromatic compounds. However‚ substitution groups affect the electrophilic substitution mechanism. A nitrogen atom attached to hydrogen is learned to be a powerful
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Bromination Solo Experiment 3 – Individual Lab Report (Save as pdf and submit‚ due by 12:00 NOON one week after experiment) Last Name: First Name: TA Name: Date Lab Performed: Date Lab Submitted: Group A‚ B‚ or C: Comments for Grading TA: (Please indicate if you performed the lab on a day other than your regularly scheduled day and/or with a TA other than your regular TA). Page Limit: report must not exceed FIVE pages (including this page) LIMIT DOES NOT INCLUDE ANY GRAPHS‚ SPECTRA
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