1. During lab, one of your classmates accidentally mixed both of their reaction mixtures, combining the benzoic acid and triphenylmethanol products (as the magnesium salts), along with the biphenyl side products (all in THF). For reasons still unknown, this classmate also added DMAP to the mixture. What advice would you give to your classmate to help them isolate both benzoic acid and triphenylmethanol, each in pure form, WITHOUT using chromatography? Use a flowchart for your answer. (HINT: biphenyl is highly soluble in hexanes, and benzoic acid, as the free acid, is insoluble in cold water. REMEMBER: THF is water-soluble) O+MgBr MgBr* biphenyl MgBr+ salt of benzoic acid MgBr+ salt of triphenylmethanol DMAP tetrahydrofuran

1. During lab, one of your classmates accidentally mixed both of their reaction mixtures, combining the benzoic acid and triphenylmethanol products (as the magnesium salts), along with the biphenyl side products (all in THF). For reasons still unknown, this classmate also added DMAP to the mixture. What advice would you give to your classmate to help them isolate both benzoic acid and triphenylmethanol, each in pure form, WITHOUT using chromatography? Use a flowchart for your answer. (HINT: biphenyl is highly soluble in hexanes, and benzoic acid, as the free acid, is insoluble in cold water. REMEMBER: THF is water-soluble) O+MgBr MgBr* biphenyl MgBr+ salt of benzoic acid MgBr+ salt of triphenylmethanol DMAP tetrahydrofuran

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter19: Enolate Anions And Enamines

Section: Chapter Questions

Problem 19.67P

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