Consider the following synthetic sequence: он A Cro/H* F CH;Br CH,MgBr E в Br2.FeBr3 G C3H,Bro Bromomethane reacts with A to generate the corresponding Grignard reagent B, which is then treated with compound C to generate the secondary alcohol D. Treatment of alcohol D with Jones reagent E results in conversion to F. Treatment of F with Br2 and a catalytic amount of FeBr3 generates the disubstituted benzene derivative G. (a) Provide the reagent A. (b) Draw the structure of reagent C. (c) Draw the structure of product F. (d) Name the type of reaction occurring in the conversion of D to F. (e) Name the type of reaction occurring in the conversion of F to G. (f) Draw the structure of product G.

Consider the following synthetic sequence: он A Cro/H* F CH;Br CH,MgBr E в Br2.FeBr3 G C3H,Bro Bromomethane reacts with A to generate the corresponding Grignard reagent B, which is then treated with compound C to generate the secondary alcohol D. Treatment of alcohol D with Jones reagent E results in conversion to F. Treatment of F with Br2 and a catalytic amount of FeBr3 generates the disubstituted benzene derivative G. (a) Provide the reagent A. (b) Draw the structure of reagent C. (c) Draw the structure of product F. (d) Name the type of reaction occurring in the conversion of D to F. (e) Name the type of reaction occurring in the conversion of F to G. (f) Draw the structure of product G.

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

Chapter10: Alcohols

Section: Chapter Questions

Problem 10.44P

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