Phenol treated with chloroform in presence of sodium hydroxide, which further hydrolysed in presence of an acid results
- Salicyclic acid
- Benzene-1,2-diol
- Benzene-1, 3-diol
- 2-Hydroxybenzaldehyde
The Correct Option is D
Approach Solution - 1
The given reaction involves the conversion of phenol to 2-Hydroxybenzaldehyde (also known as salicylaldehyde). This reaction is known as the Reimer-Tiemann reaction. Let's break down the process step-by-step:
- When phenol (C6H5OH) is treated with chloroform (CHCl3) in the presence of a strong base like sodium hydroxide (NaOH), an intermediate carbene (:CCl2) is generated. This carbene is highly reactive.
- The carbene intermediate attacks the ortho position (position 2) of the phenolic ring to form an intermediate compound.
- Subsequently, this intermediate is hydrolyzed in the presence of an acid, typically hydrochloric acid (HCl), leading to the formation of 2-Hydroxybenzaldehyde.
Thus, the treatment of phenol with chloroform and sodium hydroxide followed by hydrolysis results in the formation of 2-Hydroxybenzaldehyde.
Here's why the other options are incorrect:
- Salicyclic acid is formed by the Kolbe-Schmitt reaction and not through the Reimer-Tiemann reaction.
- Benzene-1,2-diol (catechol) and Benzene-1,3-diol (resorcinol) are different compounds that do not form under the conditions specified in the question.
The correct answer is 2-Hydroxybenzaldehyde.
Approach Solution -2
The reaction of phenol with chloroform in the presence of sodium hydroxide, followed by hydrolysis in an acidic medium, is known as the Reimer-Tiemann reaction. This reaction results in the formation of 2-hydroxybenzaldehyde (commonly known as salicylaldehyde). The reaction can be represented as:
\(\text{Phenol} + \text{CHCl}_3 + \text{NaOH} \rightarrow 2\text{-Hydroxybenzaldehyde (salicylaldehyde)}\)
The reaction involves the introduction of a formyl group (-CHO) at the ortho position relative to the hydroxyl group (-OH), producing 2-hydroxybenzaldehyde.
The Correct Answer is: 2-Hydroxybenzaldehyde
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