- A

- B

- C

- D

View written solutionFree
Correct answer: D
-
Identify the substrate
The compound is 1-methoxy naphthalene, i.e. a naphthalene ring attached to a methoxy group: where represents the 1-naphthyl group.
-
Reagent involved
Hydroiodic acid, , cleaves ethers after protonation of the oxygen atom.
-
General rule for cleavage of aryl-alkyl ethers
For an ether of the form: treatment with gives cleavage at the alkyl-O bond, not at the aryl-O bond, because:
- the bond has partial double bond character due to resonance,
- cleavage at aryl carbon by or is not feasible,
- iodide attacks the alkyl group.
-
Mechanism
First protonation of ether oxygen: \text{Ar-O-CH}_3 + H^+ \rightarrow \text{Ar-O(H)^+-CH}_3
Then iodide ion attacks the methyl group via : \text{Ar-O(H)^+-CH}_3 + I^- \rightarrow \text{Ar-OH} + CH_3I
-
Products formed
Therefore, the main products are:
- 1-naphthol
- methyl iodide
Reaction:
-
Conclusion
So the correct option must be the one corresponding to:
-
Comparison with stored answer
The stored correct answer is D. This matches the expected products for cleavage of an aryl methyl ether with HI, so I agree with the stored answer.
More from Haloalkanes and Haloarenes
- Given below are two statements : Statement I : and both can generate nucleophile. Statement II : and both will generate nitrile nucleophile with all reaction conditions. Choose the most appropriate option :2021 · MCQ
- The product formed in the first step of the reaction of with excess () is Includes diagram2021 · MCQ
- What is the major product formed by HI on reaction with Includes diagram2021 · MCQ
- Identify A and B in the chemical reaction. Includes diagram2021 · MCQ
- The given reaction can occur in the presence of : (a) Bromine water (b) in , 273 K (c) / (d) in , 273 K Choose the correct answer from the options gien below : Includes diagram2021 · MCQ
- Excess of isobutane on reaction with in presence of light at 125 C gives which one of the following, as the major product?2021 · MCQ
- The major product formed in the following reaction is : Includes diagram2021 · MCQ
- Among the following compounds I-IV, which one forms a yellow precipitate on reacting sequentially with (i) (ii) dil. (iii) ? Includes diagram2021 · MCQ