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Bromination of (E)-Stilbene & Synthesis of Diphenylacetylene

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CHEM 212
Ariel Fenster

Bromination of (E)-Stilbene & Synthesis of Diphenylacetylene Bromination of an alkene is an example of an electrophilic addition reaction. 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 1 the color or appearance of fabrics. In this experiment the stereochemi2try of bromination of (E)- stilbene is examined and synthesis of diphenylacetylene is observed. Mechanisms Data Melting point of synthesized meso-stilbene dibromide: 234-236°C 3 Literature melting point of meso-stilbene dibromide: 241°C Yield in grams: 1.0151g % yield = (100) The limiting reagent is (E)-Stilbene.2 % yield = ( ) Melting Point of synthesized diphenylacetylene: 52-55°C Literature melting point of diphenylacetylene: 59-61°C 3 Yield in grams: 0.3201g % yield ( ) ( ) ( ) 2 Limiting reagent is meso-Stilbene dibromide. Dicussion For the bromination of (E)-stilbene the results were favourable. The yield was almost 90% and the melting point was 234-236°C which is very close to the literature value of meso-stilbene 3 dibromide, which is 241°C. For the synthesis of diphenylacetylene the 3elting point was also close to the literature value, which reports a melting point of 61°C. The yield however was quite poor, only around half of the product was obtained implying a lot of the reactant was lost during the reaction. During the first part of the experiment the yield of meso-
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