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

Chemistry
10th Edition
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
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
icon
Related questions
Question
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)
о
N
MgBr+
O¯ +MgBr
Ο
N
biphenyl
MgBr* salt of
benzoic acid
MgBr+ salt of
triphenylmethanol
DMAP
tetrahydrofuran
Transcribed Image Text: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) о N MgBr+ O¯ +MgBr Ο N biphenyl MgBr* salt of benzoic acid MgBr+ salt of triphenylmethanol DMAP tetrahydrofuran
Expert Solution
steps

Step by step

Solved in 3 steps

Blurred answer
Knowledge Booster
Protection of Groups in Organic Synthesis
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY