Sign in
12thPass logo
New chatPYQ LibraryDoubtsRank report
Sign in to see Recents

Your guest activity stays on this device

Sign in to save progress →
Sign in

Haloalkanes and Haloarenes question

2021 · 18 Mar · Shift 2 · Q12
Guest · filters and generic practice availableBrowsing as a guest · PYQ filters and generic practice are available. Sign in only for personalised features and saved progress.
  1. PYQ Library
  2. /JEE Main
  3. /Chemistry
  4. /Haloalkanes and Haloarenes
  5. /2021 · 18 Mar · Shift 2 · Q12

Haloalkanes and Haloarenes question

2021 · 18 Mar · Shift 2 · Q12

JEE MainChemistryHaloalkanes and HaloarenesMCQ+4 / −1
Main products formed during a reaction of 1-methoxy naphthalene with hydroiodic acid are :
  1. A
    JEE Main 2021 (Online) 18th March Evening Shift Chemistry - Haloalkanes and Haloarenes Question 93 English Option 1
  2. B
    JEE Main 2021 (Online) 18th March Evening Shift Chemistry - Haloalkanes and Haloarenes Question 93 English Option 2
  3. C
    JEE Main 2021 (Online) 18th March Evening Shift Chemistry - Haloalkanes and Haloarenes Question 93 English Option 3
  4. D
    JEE Main 2021 (Online) 18th March Evening Shift Chemistry - Haloalkanes and Haloarenes Question 93 English Option 4
View written solutionFree

Correct answer: D

  1. Identify the substrate

    The compound is 1-methoxy naphthalene, i.e. a naphthalene ring attached to a methoxy group: Ar-O-CH3\text{Ar-O-CH}_3Ar-O-CH3​ where Ar\text{Ar}Ar represents the 1-naphthyl group.

  2. Reagent involved

    Hydroiodic acid, HI\text{HI}HI, cleaves ethers after protonation of the oxygen atom.

  3. General rule for cleavage of aryl-alkyl ethers

    For an ether of the form: Ar-O-R\text{Ar-O-R}Ar-O-R treatment with HI\text{HI}HI gives cleavage at the alkyl-O bond, not at the aryl-O bond, because:

    • the Caryl−O\text{C}_{\text{aryl}}-OCaryl​−O bond has partial double bond character due to resonance,
    • cleavage at aryl carbon by SN1S_N1SN​1 or SN2S_N2SN​2 is not feasible,
    • iodide attacks the alkyl group.
  4. 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 SN2S_N2SN​2: \text{Ar-O(H)^+-CH}_3 + I^- \rightarrow \text{Ar-OH} + CH_3I

  5. Products formed

    Therefore, the main products are:

    • 1-naphthol
    • methyl iodide

    Reaction: 1-methoxy naphthalene+HI→1-naphthol+CH3I\text{1-methoxy naphthalene} + HI \rightarrow \text{1-naphthol} + CH_3I1-methoxy naphthalene+HI→1-naphthol+CH3​I

  6. Conclusion

    So the correct option must be the one corresponding to: 1-naphthol and methyl iodide\boxed{\text{1-naphthol and methyl iodide}}1-naphthol and methyl iodide​

  7. 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.

PreviousNext

More from Haloalkanes and Haloarenes

  • Given below are two statements : Statement I : C2​H5​OH and AgCN both can generate nucleophile. Statement II : KCN and AgCN 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 Mg/Et2​O (Et=C2​H5​) 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) Br2​ in CS2​, 273 K (c) Br2​/FeBr3​ (d) Br2​ in CHCl3​, 273 K Choose the correct answer from the options gien below : Includes diagram2021 · MCQ
  • Excess of isobutane on reaction with Br2​ 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) NaOH (ii) dil. HNO3​ (iii) AgNO3​? Includes diagram2021 · MCQ