Chapter 23: Problem 592
Write the principal reaction product or products, if any, of \(0-\) cresol with \(\mathrm{CO}_{2}, \mathrm{~K}_{2} \mathrm{CO}_{3}, 240^{\circ}\)
Short Answer
Expert verified
The principal reaction product of o-cresol with CO2 and K2CO3 at 240°C is o-hydroxybenzoic acid, formed via the Kolbe-Schmitt reaction.
Step by step solution
01
Identify the reactants and reaction conditions
We have o-cresol as our main reactant, which has the chemical formula C7H8O and structure of a phenolic compound with a methyl group at the ortho position. The reaction conditions include the presence of carbon dioxide (CO2) and potassium carbonate (K2CO3) at a temperature of 240°C.
02
Determine the role of K2CO3 and CO2 in the reaction
Under the given reaction conditions, potassium carbonate (K2CO3) will first react with o-cresol to form an o-cresolate salt. This is because K2CO3, as a base, will deprotonate the acidic phenolic hydroxyl group of o-cresol. After deprotonation, the phenoxide formed can react with the carbon dioxide (CO2); the o-cresolate salt will act as a nucleophile and CO2 as an electrophile.
03
Identify the reaction type and expected product(s)
The reaction between the o-cresolate salt and CO2 under increasing temperature is known as the Kolbe-Schmitt reaction or carboxylation reaction. This type of reaction results in the formation of a salicylic acid derivative. In this particular case, with o-cresol as the starting phenol, the product will be o-hydroxybenzoic acid, along with the release of K2CO3. The overall reaction can be represented as:
o-Cresol + K2CO3 + CO2 -> o-Hydroxybenzoic acid + 2 K2CO3 (at 240°C)
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Key Concepts
These are the key concepts you need to understand to accurately answer the question.
o-cresol
o-Cresol is a type of phenol, which means it is an organic compound that contains a hydroxyl group (-OH) bonded directly to an aromatic hydrocarbon group. In the case of o-cresol, its structure features a methyl group (CH₃) attached to the benzene ring at the ortho position relative to the hydroxyl group. This arrangement is what gives o-cresol its distinct properties. Being a phenolic compound, o-cresol is slightly acidic and can participate in reactions where the hydroxyl group can donate a proton. This acidity plays an important role in many reactions, including the Kolbe-Schmitt reaction.
- Formula: C₇H₈O
- Structure: Methyl group at ortho position to the OH group
- Properties: Slightly acidic due to phenolic OH group
carboxylation reaction
The carboxylation reaction refers to a chemical reaction in which a carboxyl group (-COOH) is introduced into a molecule. This type of reaction is fundamental in organic chemistry, as it converts organic molecules into carboxylic acids. In the specific case of o-cresol, carboxylation occurs through the Kolbe-Schmitt reaction, a well-known process used to synthesize salicylic acid derivatives.
During the reaction, o-cresol first reacts with potassium carbonate to form o-cresolate, which is an intermediate phenoxide ion. This phenoxide then attacks carbon dioxide as a nucleophile. The carbon dioxide acts as an electrophile, facilitating the introduction of a carboxyl group into the aromatic ring of o-cresol.
During the reaction, o-cresol first reacts with potassium carbonate to form o-cresolate, which is an intermediate phenoxide ion. This phenoxide then attacks carbon dioxide as a nucleophile. The carbon dioxide acts as an electrophile, facilitating the introduction of a carboxyl group into the aromatic ring of o-cresol.
- Steps: Formation of o-cresolate, followed by electrophilic attack of COâ‚‚
- Products: Conversion of o-cresol into carboxylic acid derivatives
- Importance: Generates compounds with important industrial and pharmaceutical applications
o-hydroxybenzoic acid
o-Hydroxybenzoic acid is the principal product of the Kolbe-Schmitt reaction involving o-cresol. It is characterized by its chemical structure, which includes both hydroxyl and carboxyl groups attached to an aromatic benzene ring. This compound is also known as salicylic acid, a chemical widely used in the pharmaceutical industry, particularly for its role in producing aspirin and as a component in various skin care products.
- Structure: Aromatic ring with ortho OH and COOH groups
- Uses: Essential in pharmaceutical (aspirin) and cosmetic industries
- Relevance: Demonstrates the value of carboxylation in industrial chemistry