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NEET CHEMISTRYAlcohols, Phenols and EthersMedium

Question

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 (CH3COCH3CH_3-CO-CH_3). The Grignard reagent is Ethyl magnesium bromide (C2H5MgBrC_2H_5MgBr).
  2. Mechanism: The ethyl group (C2H5C_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 CH3C(OH)(CH3)CH2CH3CH_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.

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 Ethersproductformedfollowingchemicalreaction

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