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NEET CHEMISTRYMedium

The IUPAC name of the product that formed in the following chemical reaction is: Acetone →(i) C2H5MgBr, dry Ether\xrightarrow{\text{(i) } C_2H_5MgBr, \text{ dry Ether}} →(ii) H2O,H+\xrightarrow{\text{(ii) } H_2O, H^+} Product

A

Pentan-3-ol

B

2-Methylbutan-2-ol

C

2-Methylpropan-2-ol

D

Pentan-2-ol

Step-by-Step Solution

The reaction involves the nucleophilic addition of a Grignard reagent to a ketone:

  1. Reactants: Acetone is Propan-2-one (CH3−CO−CH3CH_3-CO-CH_3). The Grignard reagent is Ethyl magnesium bromide (C2H5MgBrC_2H_5MgBr).
  2. Mechanism: The ethyl group (C2H5−C_2H_5^-) from the Grignard reagent attacks the carbonyl carbon of acetone. The oxygen coordinates with MgBrMgBr. This forms an intermediate adduct. (CH3)2C=O+C2H5MgBr→(CH3)2C(OMgBr)(C2H5)(CH_3)_2C=O + C_2H_5MgBr \rightarrow (CH_3)_2C(OMgBr)(C_2H_5)
  3. Hydrolysis: Acid hydrolysis (H2O/H+H_2O/H^+) converts the adduct into a tertiary alcohol. (CH3)2C(OMgBr)(C2H5)+H2O→(CH3)2C(OH)(C2H5)+Mg(OH)Br(CH_3)_2C(OMgBr)(C_2H_5) + H_2O \rightarrow (CH_3)_2C(OH)(C_2H_5) + Mg(OH)Br
  4. Product Identification: The structure formed is CH3−C(OH)(CH3)−CH2−CH3CH_3-C(OH)(CH_3)-CH_2-CH_3. The longest carbon chain containing the -OH group has 4 carbons (Butane). The substituent is a methyl group at position 2, and the hydroxyl group is also at position 2. IUPAC Name: 2-Methylbutan-2-ol.
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