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