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NEET CHEMISTRYAlcohols, Phenols and EthersMedium

Question

A reaction between acetone and methylmagnesium chloride followed by hydrolysis will give:

A

sec-Butyl alcohol

B

tert-Butyl alcohol

C

iso-Butyl alcohol

D

iso-Propyl alcohol

Step-by-Step Solution

  1. Reactants: Acetone (CH3COCH3CH_3COCH_3) is a ketone. Methylmagnesium chloride (CH3MgClCH_3MgCl) is a Grignard reagent. The preparation of Grignard reagents (R−Mg−XR-Mg-X) is discussed in the Haloalkanes chapter .
  2. Mechanism: Grignard reagents are strong nucleophiles. The alkyl group (methyl, CH3−CH_3^-) attacks the electrophilic carbonyl carbon of the acetone.
  • Reaction: CH3−C(=O)−CH3+CH3−MgCl→(CH3)3C−OMgClCH_3-C(=O)-CH_3 + CH_3-MgCl \rightarrow (CH_3)_3C-OMgCl (Adduct formation).
  1. Hydrolysis: The intermediate adduct undergoes hydrolysis in the presence of water/acid to form an alcohol.
  • Reaction: (CH3)3C−OMgCl+H2O→(CH3)3C−OH+Mg(OH)Cl(CH_3)_3C-OMgCl + H_2O \rightarrow (CH_3)_3C-OH + Mg(OH)Cl.
  1. Product: The final product is (CH3)3C−OH(CH_3)_3C-OH, which is tert-Butyl alcohol (2-Methylpropan-2-ol). Reaction of Grignard reagents with ketones typically yields tertiary alcohols.

Exam Context & Concepts Covered

This question aligns with the NEET CHEMISTRY syllabus, specifically targeting concepts from Alcohols, Phenols and Ethers. Mastering this topic is crucial for scoring well in the upcoming medical entrance examinations. Solving conceptually related problems will help you understand the nuances of these concepts and improve your problem-solving speed.

CHEMISTRYAlcohols, Phenols and Ethersreactionbetweenacetonemethylmagnesiumchloride

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