was continued for 3h and the mixture left overnight. Remove the ethanol from the suspension with a rotary evaporator. consumed, about 12 hours. With your own solid product sample, recrystallize the solid product from aqueous 2-propanol: • Place the crude product in a 50-ml Erlenmeyer flask. The mixture is stirred about one hour at a temperature of 50-100°C, then sodium hydroxide Such reactions are shown at various places in the literature, as for ex. View desktop site, ​​​​​​Electrophilic Aromatic Iodination of Vanillin (Organic 3. Print and complete the Prelab 7 Question Sheet, and turn in at the start of lab. Watch Dr. Dan add iodine to vanillin. Set up the separatory funnel, over the stirring flask. Add 10 mL of 10% (w/w) sodium thiosulfate (Na2S2O3) solution, and then acidify with 10% (w/w) HCI, checking the acidity with pH paper. With heating, add enough 2-propanol to dissolve the solid. Next, place the ice, water bath on a stir plat and clamp the flask in the ice bath and stir. d. II. Allow the solution to cool, then place the flask in an ice bath for a few minutes before filtering once again with a clean Büchner funnel vacuum filtration setup. An ice water bath and then dissolve 1.0 g vanillin in 5-mL of ethanol in a 100-mL, round-bottomed flask with a stir bar. Iodination of vanillin and subsequent Suzuki-Miyaura coupling: two-step synthetic sequence teaching green chemistry principles. Then a solution of NaI, Vanillin (2.84 g, 20 mmole) was dissolved in 1N NaOH (20 ml) at 80°C., then a mixture of 2N (NaI, Vanillin (20 mmole) was iodinated and converted to 5-hydroxyvanillin as set forth in. Procedure: Write this in your own words; do not copy this handout! The following examples illustrate the practice of the invention.

base such as sodium hydroxide. Once the addition is complete, allow the mixture to warm to room temperature and continue to stir for 10 minutes. Vanillin (28.4 g, 200 mmole) was dissolved in 1N NaOH (200 ml) and warmed to 90°C to avoid precipitation of sodium vanillate. ring. Divide the solid product evenly between you and your groupmates. Experiment 12 Electrophilic Aromatic Iodination II.) Experiment 6: Electrophilic Aromatic Substitution: Iodination of Vanillin CHEM 336: Dr. Weiming Wu Alyssa Quinn October 22 nd, 2020 Pre-Lab: Objective: The purpose of the experiment is to perform the iodination of Vanillin with an electrophilic aromatic substitution mechanism involving sodium iodine, bleach, and ethanol. catalytic amount of sulfuric acid - preferably from 5-10 mole%. This intermediate then eliminates a leaving group, often simply a proton, to form the substituted product (Figure 1). Complete the following in your lab notebook IN PEN: a. Fourth video lab for CHM 224 and CHM 226. & the replacement of a hydrogen atom by one of the group VIIA elements) is typically carried out through the reaction of the aromatic compound with Cl2, Br, or 12, with a catalyst typically required to mediate the reaction. Expert Answer . This preview shows page 1 - 3 out of 5 pages.

Draw air through the solid product for an additional few minutes to dry. Nonetheless, aromatic halogenation is an important tool for the elaboration of aromatic compounds into specific compounds of interest or importance. This reaction is similar to an electrophilic addition reaction and occurs via two steps. Figure 1. Don't add too much 2-propanol! Although elemental iodine is relatively easy to work with, bromine is a volatile liquid, and both the liquid and the vapors can cause serious chemical burns to the skin and eyes as well as severe to fatal irritation of the respiratory passages.

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