Question Details

What is the IUPAC name of the organic compound formed in the following chemical reaction ?

Options

A

2-methyl propan-2-ol

B

pentan-2-ol

C

pentan-3-ol

D

2-methyl butan-2-ol

Show Answer

Correct Answer :

Option D

2-methyl butan-2-ol

2-methyl butan-2-ol

Solution :

The correct answer is 2-methyl butan-2-ol.

Step-by-Step Explanation:

1. Identify the Reactants:
- Acetone (Propan-2-one): A ketone with the chemical structure CH3-CO-CH3 containing a highly polar carbonyl group (C=O).
- Ethylmagnesium bromide (C2H5MgBr): A Grignard reagent that serves as a source of the nucleophilic ethyl group (C2H5-).

2. Step 1: Nucleophilic Addition of Grignard Reagent:
The nucleophilic ethyl group (C2H5-) attacks the electrophilic carbonyl carbon of acetone in dry ether. The electron pair from the C=O double bond shifts to the oxygen atom, forming a magnesium salt intermediate:
(CH3)2C=O+C2H5MgBr(CH3)2C(OMgBr)(C2H5)

3. Step 2: Acid Hydrolysis:
Subsequent protonation/hydrolysis of the alkoxide intermediate with water in an acidic medium (H2O/H+) yields a tertiary alcohol:
(CH3)2C(OMgBr)(C2H5)+H2O(CH3)2C(OH)(C2H5)+Mg(OH)Br

4. IUPAC Nomenclature of the Product:
- The structure of the resulting alcohol is:
CH3-CH2-C(OH)(CH3)2
- The longest continuous carbon chain containing the hydroxyl (-OH) group has 4 carbon atoms, which corresponds to butane.
- Numbering the chain from the right side gives the lowest locants to the substituents:
  • C1: -CH3 (terminal right)
  • C2: Carbon bonded to both the -OH group and a methyl (-CH3) substituent
  • C3: -CH2-
  • C4: -CH3 (terminal left)
- Combining these substituent locations, we have a methyl group at carbon-2 and the alcohol group at carbon-2.
- Therefore, the IUPAC name is 2-methyl butan-2-ol.

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