A Grignard reaction of phenylmagnesium bromide with 3-pentanone gives 3-phenylpentan-3-ol as the major product. The crude product contains the 3-phenylpentan-3-ol product, unreacted 3-pentanone, and biphenyl (a side product). A developing solvent is found that separates the mixture into three spots on a silica gel TLC plate. Considering the functional groups present, predict which compounds would have the smallest and largest Rf values. Briefly justify your answer.

A Grignard reaction of phenylmagnesium bromide with 3-pentanone gives 3-phenylpentan-3-ol as the major product. The crude product contains the 3-phenylpentan-3-ol product, unreacted 3-pentanone, and biphenyl (a side product). A developing solvent is found that separates the mixture into three spots on a silica gel TLC plate. Considering the functional groups present, predict which compounds would have the smallest and largest Rf values. Briefly justify your answer.

EBK A SMALL SCALE APPROACH TO ORGANIC L

4th Edition

ISBN:9781305446021

Author:Lampman

Publisher:Lampman

Chapter59: Preparation Of A C-4 Or C-5 Acetate Ester

Section: Chapter Questions

Problem 2Q

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