Synthesis Of Ethyl Cinnamate Lab Report

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The Synthesis of Ethyl-2, 3-dibromo-3-phenylpropionate via Bromination of Ethyl Cinnamate Introduction Organic synthesis is a scientific field that goes unappreciated in the world. When hearing those two words, most people turn their heads without realizing the importance the field has on their everyday lives. This field and the scientists who are brave enough to partake in organic synthesis, make medicines, catalysts and chemicals that are found in most modern day objects. Organic synthesis uses numerous reactions to create these products; one very important reaction used during organic synthesis is known as an alkene addition reaction. An alkene addition reaction occurs when an electrophile bonds to the pi bond on an alkene. The pi bond between the carbons of the alkene breaks, and then attaches to the electrophile. During the addition of the electrophile, the reagent carrying it would then attach to the open…show more content…
Ethyl cinnamate (0.15 g, 2.84 mmol) and 200 proof ethanol (15 mL) was added to a round-bottom flask and stirred continuously. Hydrobromic acid (4 mL) was then slowly added to the reaction mixture. The mixture was then heated to level 50 on the varistat and stirred for ten minutes. 30% hydrogen peroxide (4 mL) was added dropwise to the reaction mixture. The reaction mixture was heated at level 50 on the varistat for 60 minutes and was monitored by TLC (30% hexanes with 70% ethyl acetate). Upon completion, the reaction mixture was neutralized with concentrated sodium bicarbonate (10M), and then the water and bromine was removed by vacuum filtration to yield white cloudy crystals. Recrystallization using 95% ethanol (25 mL) yielded a cloudy mixture. The 95% ethanol was removed by vacuum filtration, which afforded white crystals (0.641 g, 67.5%) mp: 66.5-68.3 ⁰C; 1H NMR (60 Mhz, CDCl3): đ (ppm) 1.4 (t, 3H), 4.4 (q, 2H), 4.7 (d, 1H), 5.2 (d, 2H), 7.4 (s, 5H); IR (ATR) ymax (cm-1) 3377.5, 1728.5, 1271.3, 599.2,

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