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Q.Carry out the following conversion: Propan-2-one → 2-Methylpropan-2-ol
Tripura TbseHigher Secondary (+2 Stage) Examination 2024Subjective· 1mImportance★★★★★
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Start your 14-day free trial to unlock the full solution →Adding a methyl Grignard reagent to acetone, then hydrolysing, converts the ketone's C=O into a C–OH bearing an extra methyl group — giving the tertiary alcohol 2-methylpropan-2-ol directly.
Step 1: Propan-2-one (acetone) reacts with methylmagnesium bromide (a Grignard reagent). The nucleophilic methyl carbanion (from CH3MgBr) adds across the carbonyl carbon of acetone, giving a magnesium alkoxide intermediate:
CH3COCH3 + CH3MgBr → (CH3)3C–OMgBr
Step 2: Hydrolysis of this alkoxide with dilute acid (H3O+) liberates the tertiary alcohol:
(CH3)3C–OMgBr + H3O+ → (CH3)3C–OH + Mg(OH)Br
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