NOC↔XT Ph CI Ph `ОН Acid chlorides react with Grignard reagents to yield tertiary alcohols, two equivalents of Grignard reagent are required. The first equivalent reacts in a typical nucleophilic acyl substitution reaction to give a ketone. This ketone, however, is itself reactive in the Grignard reaction. Thus, the second equivalent adds to the ketone carbonyl carbon. Subsequent protonation yields the tertiary alcohol. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Ph :0: 1. 2 eq. CH₂MgBr 2. H3O+ CH3 H3C CH3 H3C-MgBr Ph + O: MgBr CH3 CH3
NOC↔XT Ph CI Ph `ОН Acid chlorides react with Grignard reagents to yield tertiary alcohols, two equivalents of Grignard reagent are required. The first equivalent reacts in a typical nucleophilic acyl substitution reaction to give a ketone. This ketone, however, is itself reactive in the Grignard reaction. Thus, the second equivalent adds to the ketone carbonyl carbon. Subsequent protonation yields the tertiary alcohol. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Ph :0: 1. 2 eq. CH₂MgBr 2. H3O+ CH3 H3C CH3 H3C-MgBr Ph + O: MgBr CH3 CH3
Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions
Section19.SE: Something Extra
Problem 28VC
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