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

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Chapter1: Chemical Foundations
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NAC↔X™
Ph
Ph
OH
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. CH3MgBr
2. H3O+
CH3
H3C CH3
H3C-MgBr
Ph
O: MgBr
-CH3
CH3
Transcribed Image Text:NAC↔X™ Ph Ph OH 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. CH3MgBr 2. H3O+ CH3 H3C CH3 H3C-MgBr Ph O: MgBr -CH3 CH3
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