Question Details

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


Options

A

pentan-3-ol

B

2-methyl butan-2-ol

C

2-methyl propan-2-ol

D

pentan-2-ol

Show Answer

Correct Answer :

Option B

2-methyl butan-2-ol

Solution :

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


Analysis of the Chemical Reaction:

As seen in the provided image:

The chemical reaction involves the reaction of Acetone with ethylmagnesium bromide (C2H5MgBr), a Grignard reagent, in dry ether, followed by acidic hydrolysis (H2O,H+).


Step-by-Step Reaction Mechanism:

Step 1: Nucleophilic Addition of Grignard Reagent
Acetone is a ketone with the formula CH3-CO-CH3 (propan-2-one). The ethyl group (C2H5-) of ethylmagnesium bromide acts as a nucleophile and attacks the electrophilic carbonyl carbon atom of acetone, opening the carbon-oxygen double bond to form a magnesium alkoxide complex adduct.

CH3-CO-CH3+C2H5MgBr(CH3)2C(C2H5)-O-MgBr+


Step 2: Acid Hydrolysis
Protonation of the alkoxide adduct via treatment with dilute acid (H2O/H+) yields a tertiary alcohol:

(CH3)2C(C2H5)-O-MgBr+H2O/H+CH3-C(OH)(CH3)-CH2-CH3+Mg(OH)Br


IUPAC Naming of the Product:
The resulting alcohol structure is CH3-C(OH)(CH3)-CH2-CH3.
1. The longest continuous carbon chain containing the hydroxyl functional group (-OH) consists of 4 carbon atoms, which makes the parent alkane butane.
2. Numbering the chain from the end closest to the -OH group gives the carbon carrying the -OH group position 2.
3. There is a methyl substituent (-CH3) also attached to position 2.
4. Thus, the systematic IUPAC name of the formed organic compound is 2-methyl butan-2-ol.

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