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Predict the major organic product of the following reaction sequence. Styrene (1.53 g, 0.011 mol) in methanol (30 mL) was added to a mixture of Hg(OAc)2 (5.30 g, 0.016 mol) in methanol (100 mL) at room temp. and stirred for 24 h. Sodium hydroxide (3.0 M, 16 mL) was added, followed by NaBH4 (0.32 g, 0.008 mol) in NaOH (3.0 M, 16 mL) at 0 °C. The precipitated Hg was removed by filtration. The product was isolated by diethyl ether extraction. After drying over NazSO4, solvent was removed and distillation gave the product. (Adapted from: Senda, Y.; Kanto, H.; Itoh, H. J. Chem. Soc., Perkin Trans. 2 1997, 1143-1146.)

Predict the major organic product of the following reaction sequence. Styrene (1.53 g, 0.011 mol) in methanol (30 mL) was added to a mixture of Hg(OAc)2 (5.30 g, 0.016 mol) in methanol (100 mL) at room temp. and stirred for 24 h. Sodium hydroxide (3.0 M, 16 mL) was added, followed by NaBH4 (0.32 g, 0.008 mol) in NaOH (3.0 M, 16 mL) at 0 °C. The precipitated Hg was removed by filtration. The product was isolated by diethyl ether extraction. After drying over NazSO4, solvent was removed and distillation gave the product. (Adapted from: Senda, Y.; Kanto, H.; Itoh, H. J. Chem. Soc., Perkin Trans. 2 1997, 1143-1146.)

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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Predict the major organic product of the following reaction sequence. Styrene (1.53 g, 0.011 mol) in methanol (30 mL) was added to a mixture of Hg(OAc)2 (5.30 g, 0.016 mol) in methanol (100 mL) at room temp. and stirred for 24 h. Sodium hydroxide (3.0 M, 16 mL) was added, followed by NaBH4 (0.32 g, 0.008 mol) in NaOH (3.0 M, 16 mL) at 0 °C. The precipitated Hg was removed by filtration. The product was isolated by diethyl ether extraction. After drying over NazSO4, solvent was removed and distillation gave the product. (Adapted from: Senda, Y.; Kanto, H.; Itoh, H. J. Chem. Soc., Perkin Trans. 2 1997, 1143-1146.)
Transcribed Image Text:Predict the major organic product of the following reaction sequence. Styrene (1.53 g, 0.011 mol) in methanol (30 mL) was added to a mixture of Hg(OAc)2 (5.30 g, 0.016 mol) in methanol (100 mL) at room temp. and stirred for 24 h. Sodium hydroxide (3.0 M, 16 mL) was added, followed by NaBH4 (0.32 g, 0.008 mol) in NaOH (3.0 M, 16 mL) at 0 °C. The precipitated Hg was removed by filtration. The product was isolated by diethyl ether extraction. After drying over NazSO4, solvent was removed and distillation gave the product. (Adapted from: Senda, Y.; Kanto, H.; Itoh, H. J. Chem. Soc., Perkin Trans. 2 1997, 1143-1146.)
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