Q15.113CP - Chemistry: Molecular Nature Of Matter And Change

Question

Question: Ibuprofen is one of the most common anti-inflammatory drugs. 

(a) Identify the functional group(s) and chiral center(s) in ibuprofen. 

(b) Write a four-step synthesis of a racemic mixture of ibuprofen from 4-isobutyl benzaldehyde, using inorganic reactants and one organometallic reactant (see Problem 15.107).

Step-by-Step Solution

Answer

Answer

1. Ibuprofen has a carboxylic acid and two chiral centers.

2.Mechanism followed as:

Step 1: Functional group

These are the different groups concerning molecules present in molecules having other chemical properties irrespective of the molecule’s atoms.

Like ibuprofen, it has a carboxylic group -COOH group in the substituted chain.

Step 2: Chiral center

The chiral centres are the carbon that forms four bonds with different atoms. All four atoms are distinct from each other, called chiral atoms. So, ibuprofen has two chiral atoms, as shown below:

Step 3: Formation of ibuprofen from 4-isobutyl benzaldehyde

Four-step synthesis followed as follows;

1. 4-isobutyl benzyl aldehyde reacts with NaOEt
2. Followed by hydrolysis
3. Acylation is done from nitrile
4. Followed by hydrolysis