Question

Among the given options, the possible product(s) that can be obtained from the following reaction is/are: 

• A.
• B.
• C.
• D.

Hint:

In the Reimer–Tiemann reaction, activated aromatic systems with electron-donating groups can react with chloroform and base to form ortho-formylated or chlorinated ketone products depending on the aromatic structure.

Answer 1

The Correct Option is A

The given reaction is a Reimer–Tiemann reaction, where an electron-donating group (such as –OMe) on an aromatic ring undergoes formylation at the ortho-position using chloroform (CHCl₃) and aqueous NaOH under heat.

However, the structure here is 1-methoxynaphthalene, not a simple phenol. In such naphthalene systems, the Reimer–Tiemann conditions lead to a reaction at the activated ortho-position (with respect to the methoxy group), generating an intermediate dichlorocarbene which reacts and ultimately introduces a –CHO group ortho to the OMe group, then oxidized under the conditions to a formyl derivative or rearranges.

But due to the extended conjugation and stability in naphthyl systems, halogenated ketone derivatives like (A) are known to form instead. This compound is a result of electrophilic substitution at the activated site followed by oxidation.

Let’s evaluate the options:

• (A) Matches the expected product from the reaction of 1-methoxynaphthalene with CHCl₃/NaOH. CORRECT
• (B) Shows hydroxyl substitution not expected under Reimer–Tiemann. WRONG
• (C) Represents an unreactive dichlorocarbene adduct without oxidation—unlikely major product. WRONG
• (D) Suggests formylation at a distant site; incorrect regioselectivity. WRONG

\[ \boxed{\text{Correct product is (A)}} \]