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

Correct Answer :

2-methyl butan-2-ol

Solution :

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

Step-by-step explanation:

1. Identify the reactants from the given image:
The chemical reaction shown in the image starts with Acetone, which is reacted with:
(i) Ethylmagnesium bromide (C2H5MgBr, a Grignard reagent) in the presence of dry ether.
(ii) Water in acidic medium (H2O,H+) for hydrolysis.

2. Mechanism of the Reaction:
Step 1: Nucleophilic Addition
Acetone contains a polar carbonyl group (C=O):
CH3-CO-CH3
The nucleophilic ethyl group (-C2H5) from the Grignard reagent attacks the electrophilic carbonyl carbon of acetone. Simultaneously, the pi-electrons of the carbonyl bond shift to the oxygen atom, forming a magnesium halide adduct:
(CH3)2C=O+C2H5MgBr(CH3)2C(OMgBr)(C2H5)

Step 2: Hydrolysis
Acidic hydrolysis of the adduct protonates the oxygen atom to yield a tertiary alcohol:
(CH3)2C(OMgBr)(C2H5)+H2OH+(CH3)2C(OH)(C2H5)+Mg(OH)Br

3. IUPAC Nomenclature of the Product:
The structure of the product is:
CH3-C(OH)(CH3)-CH2-CH3
• Find the longest continuous carbon chain containing the carbon atom bonded to the hydroxyl group (-OH). This chain has 4 carbon atoms, which corresponds to butane.
• Number the chain from the end closer to the hydroxyl group (from left to right):
- C-1: -CH3 (leftmost methyl group)
- C-2: Carbon with both the -OH group and a methyl (-CH3) substituent
- C-3: -CH2-
- C-4: -CH3 (rightmost ethyl carbon)
• The hydroxyl group is at C-2, which gives the parent suffix butan-2-ol.
• The methyl substituent is also attached to C-2, giving the prefix 2-methyl.
• Therefore, the IUPAC name of the compound is 2-methyl butan-2-ol.

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