A chemist was charged with the task of making amino alcohol 2. This chemist decided to attempt a Grignard reaction between two equivalents of phenylmagnesium bromide and amino ester 1. To this end, two equivalents of the Grignard reagent were added to a flask containing a stirred THF solution of ester 1 at -78 °C. Upon acidic aqueous work-up of the reaction mixture, the desired alcohol 2 was not isolated, even though one equivalent of methanol was produced and all the starting materials were consumed. Instead, two products with the molecular formulae of C6H6 and C7H13NO were obtained in a 2:1 ratio, respectively. Identify the structures of these two products and describe, mechanistically, how they were formed. MgBrMeOO Me Me(2 equivalents)1Me Me+MeOHноNH2NH22

The objective of the question is to identify the structures of the two products formed in a Grignard…

Answered: MgBr MeO O Me Me (2 equivalents) 1 Me…

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...

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A chemist was charged with the task of making amino alcohol 2. This chemist decided to attempt a Grignard reaction between two equivalents of phenylmagnesium bromide and amino ester 1. To this end, two equivalents of the Grignard reagent were added to a flask containing a stirred THF solution of ester 1 at -78 °C. Upon acidic aqueous work-up of the reaction mixture, the desired alcohol 2 was not isolated, even though one equivalent of methanol was produced and all the starting materials were consumed. Instead, two products with the molecular formulae of C₆H₆ and C₇H₁₃NO were obtained in a 2:1 ratio, respectively. Identify the structures of these two products and describe, mechanistically, how they were formed.