2. 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. MgBr + MeO (2 equivalents) O Me Me 1 Me Me HO + MeOH NH2 NH₂ 2

2. 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. MgBr + MeO (2 equivalents) O Me Me 1 Me Me HO + MeOH NH2 NH₂ 2

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 19.37P

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