Question

Which cannot be used as a ' \(\mathrm{X}\) ' in following reaction? (A) Jones reagent (B) Tollen's reagent followed by \(\mathrm{H}^{+}\) (C) COC(=O)c1ccccc1 (D) \(\mathrm{H}_{5} \mathrm{IO}_{6}\)

Short answer

Option C: Benzyl Methyl Ketone cannot be used as 'X' in the reaction, as it is not an oxidizing agent.

Step-by-step solution

Option A: Jones Reagent

Jones reagent is a mixture of chromic anhydride and dilute sulfuric acid, which is widely used in organic chemistry as an oxidizing agent. It can perform oxidation of various organic compounds. It can work as 'X' in a reaction.

Option B: Tollen's Reagent followed by \(\mathrm{H}^{+}\)

Tollen's reagent is an ammoniacal silver nitrate solution, which is mainly used as an oxidizing agent to oxidize aldehydes. This reagent can also be used as 'X' in a reaction when followed by \(\mathrm{H}^{+}\), as it helps in the oxidation process.

Option C: COC(=O)c1ccccc1

The SMILES code provided here represents a specific molecule called Benzyl Methyl Ketone. This compound is not known to be an oxidizing agent or be used as 'X' in a reaction. Hence, it cannot be used as a 'X' in the reaction.

Option D: \(\mathrm{H}_{5} \mathrm{IO}_{6}\)

\(\mathrm{H}_{5} \mathrm{IO}_{6}\) is an iodic acid salt, which can act as a strong oxidizing agent due to the presence of iodine in its highest oxidation state (+7). Therefore, it can be used as 'X' in a reaction. In conclusion, our analysis shows that the molecule represented by the SMILES code in Option C cannot be used as 'X' in the following reaction.

Key concepts

Jones reagent

Jones reagent is a powerful oxidizing agent used extensively in organic chemistry. It consists of chromic anhydride
dissolved in dilute sulfuric acid. This combination is particularly effective at oxidizing alcohols, converting primary alcohols into carboxylic acids, and secondary alcohols into ketones.

• Properties: Deep orange/red color, due to the chromic acid component.
• Applications: Commonly used in laboratory settings for the oxidation of alcohols to enhance their functional group transformations.

Understanding the role of Jones reagent in organic transformations is crucial for appreciating how oxidative processes can be carefully controlled to yield specific products.

Tollen's reagent

Tollen's reagent is another oxidizing agent, best known for its use in the "silver mirror test." It is a solution of silver nitrate (
AgNO₃) in ammonia.

• Function: It selectively oxidizes aldehydes to carboxylic acids, while leaving ketone groups unchanged.
• Testing: The formation of a silver mirror on the inner surface of a test tube indicates the presence of aldehyde groups.

This reagent is vital in differentiating between aldehydes and ketones because ketones do not react, making Tollen's reagent highly valued in organic testing environments.

Benzyl Methyl Ketone

This compound, represented in SMILES notation as COC(=O)c1ccccc1, acts as neither a reagent nor an agent
in oxidation reactions. Benzyl Methyl Ketone is primarily a ketone, a type of organic compound characterized by a carbonyl group
(C=O) bonded to two carbon atoms.

• Structure: Consists of a phenyl group attached to an acetyl group.
• Usage: Often used as an intermediate in the synthesis of pharmaceuticals and various organic compounds.

Due to its neutral role in oxidation, Benzyl Methyl Ketone is unsuitable as an oxidative component in typical reactions.

iodic acid

Iodic acid, represented by the formula
off{ balances well as an oxidizing agent in organic chemistry. It can effectively oxidize a variety of substrates owing to iodine's high
involvement in increasing oxidation states.

• Properties: Appears as a white crystalline solid, stable, and relatively soluble in water.
• Reactivity: Often used to cleave vicinal diols into aldehyde products.

Iodic acid's ability to participate in significant redox reactions makes it invaluable for certain oxidative pathways in organic synthesis.

SMILES notation

SMILES (Simplified Molecular Input Line Entry System) is a way of representing molecular structures using short strings of text. This notation is a powerful tool in computational chemistry and cheminformatics.

• Purpose: Encodes the structure of molecules in a text form that can be easily read by humans and computers.
• Utility: Facilitates the sharing and searching of complex molecular structures across chemical databases.

SMILES notation helps chemists and computer scientists in efficiently communicating intricate molecular structures without the need for graphical representations.