Q.Why is it necessary to avoid even traces of moisture during the use of a Grignard reagent?
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Start your 14-day free trial to unlock the full solution →Step 1. The Grignard reagent's carbon is strongly nucleophilic/carbanion-like (R delta- - Mg delta+ - X), and RMgX is also a very strong base.
Step 2. Water, alcohols and amines all carry an 'active' (acidic-enough) hydrogen. If even a trace of any of these is present, RMgX instantly abstracts that proton, exactly as in reaction 10 of its synthetic uses: RMgX + H-OH gives R-H + Mg(OH)X.
Step 3. This side reaction converts the valuable, versatile Grignard reagent into the simple, synthetically useless alkane R-H -- and it happens far faster than the reagent's intended reaction with the actual target substrate (a carbonyl compound, CO2, etc.), so even a small amount of moisture can quietly consume most of the reagent before the real reaction ever gets a chance. …
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