8. Under anhydrous conditions, 4.8 mL of 1-bromo-3,5-dimethylbenzene (dens. 1.36 g/mL) is treated with 0.90 g of magnesium in 25 mL of diethyl ether. After the initial reaction, the ether solution is poured over 8.5 grams of dry ice (carbon dioxide). The mixture is then treated with 50 mL 1M aqueous HCl. The resulting biphasic mixture is transferred to a separatory funnel and the aqueous layer is removed. The organic layer that remains in the separatory funnel is then treated with 20 mL 3M aqueous NaOH. After shaking the separatory funnel and allowing the layers to separate, the aqueous layer is removed and treated with aqueous 6M HCl until a precipitate forms and the pH of the solution acidic by pH paper. The precipitate is isolated by vacuum filtration and allowed to dry resulting in 3.73 g of a white solid (m. p. 171.2 – 173.4 C). Assuming the product is 3,5-dimethylbenzoic acid, calculate the percent yield. Br 1) Mg°, Et,0 ОН 2) СО2 3) H* 1-bromo-3,5-dimethylbenzene 3,5-dimethylbenzoic acid

8. Under anhydrous conditions, 4.8 mL of 1-bromo-3,5-dimethylbenzene (dens. 1.36 g/mL) is treated with 0.90 g of magnesium in 25 mL of diethyl ether. After the initial reaction, the ether solution is poured over 8.5 grams of dry ice (carbon dioxide). The mixture is then treated with 50 mL 1M aqueous HCl. The resulting biphasic mixture is transferred to a separatory funnel and the aqueous layer is removed. The organic layer that remains in the separatory funnel is then treated with 20 mL 3M aqueous NaOH. After shaking the separatory funnel and allowing the layers to separate, the aqueous layer is removed and treated with aqueous 6M HCl until a precipitate forms and the pH of the solution acidic by pH paper. The precipitate is isolated by vacuum filtration and allowed to dry resulting in 3.73 g of a white solid (m. p. 171.2 – 173.4 C). Assuming the product is 3,5-dimethylbenzoic acid, calculate the percent yield. Br 1) Mg°, Et,0 ОН 2) СО2 3) H* 1-bromo-3,5-dimethylbenzene 3,5-dimethylbenzoic acid

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter3: Organic Compounds: Alkanes And Their Stereochemistry

Section3.SE: Something Extra

Problem 50AP: Formaldehyde, H2C=O, is known to all biologists because of its usefulness as a tissue preservative....

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