Target Exam

CUET

Subject

Chemistry

Chapter

Organic: Alcohols, Phenols and Ethers

Question:

The major product of Kolbe's reaction is used for the synthesis of a precursor substrate in the preparation of aspirin. The electrophile used in Kolbe's reaction is

Options:

Carbon dioxide

Carbon monoxide

Acetic anhydride

Phenol

Correct Answer:

Carbon dioxide

Explanation:

The correct answer is Option (1) → Carbon dioxide

1. The Reaction:

The Kolbe reaction (also known as the Kolbe-Schmitt reaction) is the chemical reaction of sodium phenoxide (the salt of phenol) with carbon dioxide under heat and pressure.

  • Substrate (Nucleophile): Phenoxide ion (derived from phenol). The negative charge on the oxygen makes the ring highly electron-rich.
  • Reagent (Electrophile): Carbon dioxide ($\text{CO}_2$). Although $\text{CO}_2$ is a weak electrophile, the strong nucleophilic nature of the phenoxide ion allows the reaction to proceed.

2. The Product and Aspirin Synthesis:

The major product of this reaction is salicylic acid (2-hydroxybenzoic acid). As mentioned in your prompt, salicylic acid is the precursor used to make aspirin.

  • Step 1 (Kolbe's Reaction):

$\text{Phenol} \overset{\text{NaOH}}{\longrightarrow} \text{Sodium Phenoxide} \overset{\text{CO}_2, \text{ H}^+}{\longrightarrow} \text{Salicylic Acid}$

  • Step 2 (Acetylation):

Salicylic acid is then treated with acetic anhydride to produce Aspirin (Acetylsalicylic acid).

Why the other options are incorrect:

  • Carbon monoxide: Used in reactions like the Gattermann-Koch reaction to form aldehydes, not in Kolbe's reaction.
  • Acetic anhydride: This is the electrophile used in the next step (acetylation) to convert salicylic acid into aspirin, but it is not used in the Kolbe reaction itself.
  • Phenol: This is the starting material (substrate) that acts as the nucleophile, not the electrophile.