Problem 52 - Arihant Objective Approach to Organic Chemistry for IIT JEE and NEET all Medical Entrances Part 4

Question

O=C(O)c1ccc(O)cc1 \(X\) is identified as (a) \(2,4,6\)-tribromophenol (b) 2-bromo-4-hydroxylbenzene sulphonic acid (c) 3,5-dibromo-4-hydroxybenzene sulphonic acid (d) 2-bromophenol

Step-by-Step Solution

Answer

The SMILES does not match any options provided.

Step 1: Identify the Structure from SMILES

The SMILES string provided is 'O=C(O)c1ccc(O)cc1', which represents the structure of benzoic acid. This structure consists of a benzene ring with a carboxylic acid group (COOH) and a hydroxyl group (OH) attached.

Step 2: Analyze the Options Provided

The options given include different brominated phenols and sulphonic acids. We need to determine which of these matches our identified SMILES structure. Since the SMILES corresponds to benzoic acid with a phenolic group, we examine each answer choice for a match with this basic configuration.

Step 3: Compare Options with Identified Structure

None of the options directly corresponds to the SMILES representation of benzoic acid. They are all brominated or have sulphonic groups, whereas the SMILES has no bromine or sulphonic groups. - (a) 2,4,6-tribromophenol has three bromines and a phenol group. - (b) 2-bromo-4-hydroxylbenzene sulphonic acid has one bromine, a phenol group, and a sulphonic acid group. - (c) 3,5-dibromo-4-hydroxybenzene sulphonic acid has two bromines, a phenol group, and a sulphonic acid group. - (d) 2-bromophenol has one bromine and a phenol group. None match the benzoic acid structure with a single hydroxyl group.

Step 4: The Conclusion

Upon further examination, the SMILES string provided does not include any bromine atom nor sulphonic acid group. It actually corresponds to salicylic acid, which doesn't match any of the options provided. Thus, none of the given answer options (a)-(d) match the provided SMILES structure.

Key Concepts

benzoic acid

Benzoic acid is a simple aromatic carboxylic acid characterized by a distinct benzene ring. This ring is lined with a \( \text{COOH} \) group, commonly referred to as the carboxylic acid group. Benzoic acid is a highly stable structure due to the delocalization of electrons in the benzene ring.
In terms of chemistry:

• Benzoic acid serves as a precursor for manufacturing various organic compounds.
• It is primarily known for its role as a food preservative, under the name E210.
• This compound can be synthesized through the oxidation of toluene.

Moreover, benzoic acid's structure is relatively simple, making it a favorite topic in organic chemistry courses when learning about aromatic compounds and their derivatives.

salicylic acid

Salicylic acid is an organic compound that shines in both medical and chemical fields. Its structure consists of a benzene ring with two functional groups: a hydroxyl group \( (\text{OH}) \) at the para-position and a carboxylic acid group \( (\text{COOH}) \). This setup is what the SMILES string 'O=C(O)c1ccc(O)cc1' represents.
Salicylic acid is best known for:

• Its use in skincare products where it helps to treat acne by exfoliating the skin.
• Its role in the synthesis of aspirin (acetylsalicylic acid).
• Functioning as a plant hormone that plays a vital role in plant growth and development.

The dual presence of hydroxyl and carboxyl groups makes it more versatile in chemical reactions than simple benzoic acid.

organic chemistry

Organic chemistry is a vast branch of chemistry focused on the study of carbon-containing compounds. These compounds are everywhere around us, from the food we eat to the clothes we wear.
Key aspects of organic chemistry include:

• The ability to understand and manipulate the structures, properties, and reactions of organic substances.
• The exploration of functional groups, which are specific groupings of atoms within molecules that dictate their reactivity and properties.
• The use of techniques like SMILES (Simplified Molecular Input Line Entry System) to represent molecules. SMILES helps to digitally communicate complex structures like benzoic and salicylic acid.

Organic chemistry forms the backbone of many industries, including pharmaceuticals, agriculture, and materials science. Through the lens of organic chemistry, we can transform simple raw materials into valuable products.