Skip to content
Question 52 of 76

Q.Alcohols cannot be used as a solvent for Grignard reagent. Give reason.

Puducherry TnboardTamil Nadu HSC (DGE) Board 2017Subjective· 3mImportance★★★★★
68% · 52/76 Questions
🔒 Locked · start free trial →

You're viewing a preview — the full solution, concept, methods & PYQ mapping are locked.

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 −OH-OH 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, RMgXRMgX, has a highly polar Rδ−−Mgδ+XR^{\delta-}-Mg^{\delta+}X 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 −OH-OH (alcohols, water), −COOH-COOH, −NH2-NH_2/−NH−-NH-, or terminal alkyne ≡C−H\equiv C-H.

If an alcohol, R′OHR'OH, were used as the solvent, the Grignard reagent would react with the solvent itself as fast as it formed:

RMgX+R′OH→R−H↑+R′−O−MgXRMgX + R'OH \rightarrow R-H\uparrow + R'-O-MgX

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 CO2CO_2.

Why dry ether is used instead: Diethyl ether (C2H5−O−C2H5C_2H_5-O-C_2H_5) is chosen as the solvent because:

  • It has no active/acidic hydrogen, so it does not react with the Grignard reagent. …

Unlock everything free for 14 days

  • Full step-by-step solutions
  • Concept-first explanations
  • Methods, shortcuts & mistakes
  • PYQ mapping + timed mock tests

Full access for 14 days. No credit card required.