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Questions

CHE 008B A01 SS1 2025 Lecture 13 - Reactions of Acyl Halides

Multiple fill-in-the-blank

Reaction of an acyl halide with an organolithium then acidic work up requires [Fill in the blank], equivalents of organolithium reagent. We'll form a [Fill in the blank], functional group intermediate by a [Fill in the blank], , and then a [Fill in the blank], functional group intermediate by a [Fill in the blank], and finally acid work up gives a [Fill in the blank], .  

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Step-by-Step Analysis
First, let's lay out the sequence described in the prompt and the provided fill-ins so we can assess each statement. Step 1: Reagent equivalents. The claim is that the reaction requires 2 equivalents of organolithium reagent. In this two-step process, the first equivalent performs a nucleophilic acyl substitution on the acyl halide to give a ketone intermediate, and the second equivalent adds to that ketone to form the alkoxide. Therefore, using two equivalents is consistent with generating both the ketone and then the tertiary alcohol upon workup. If only one equivalent were used, you would generally stop at the ketone or fail to drive the second additi......Login to view full explanation

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