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NEET CHEMISTRYMedium

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.
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