Q.Alcohols cannot be used as a solvent for Grignard reagent. Give reason.
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Start your 14-day free trial to unlock the full solution →Grignard reagents are powerful carbanion-like nucleophiles/bases that react instantly with any active hydrogen; the hydrogen of an alcohol is active, so an alcohol solvent would consume the Grignard reagent before it ever meets the desired substrate.
Reason: The Grignard reagent, , has a highly polar bond, giving the carbon a strong carbanion-like (basic/nucleophilic) character. It reacts violently and instantaneously with any compound containing an active (i.e. sufficiently acidic) hydrogen atom, such as the hydrogen of (alcohols, water), , /, or terminal alkyne .
If an alcohol, , were used as the solvent, the Grignard reagent would react with the solvent itself as fast as it formed:
This protonates the carbanion-like carbon, converting the valuable Grignard reagent into a simple alkane (wasting it) and an alkoxymagnesium halide — leaving no active Grignard reagent to carry out the desired addition reaction with, say, an aldehyde, ketone, ester, or .
Why dry ether is used instead: Diethyl ether () is chosen as the solvent because:
- It has no active/acidic hydrogen, so it does not react with the Grignard reagent. …
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