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NEET CHEMISTRYAlcohols, Phenols and EthersMedium

Question

Among the following ethers, the one that will produce methyl alcohol on treatment with hot concentrated HI is:

A

Option 1

B

Option 2

C

Option 3

D

tert-butyl methyl ether

Step-by-Step Solution

The reaction of ethers with hot concentrated HI involves the cleavage of the C-O bond. The mechanism depends on the nature of the alkyl groups attached to the oxygen.

  1. General Rule (SN2): For primary or secondary alkyl groups, the iodide ion (II^-) is a strong nucleophile and attacks the less sterically hindered alkyl group. In a methyl ether (ROCH3R-O-CH_3), II^- would typically attack the methyl group to form methyl iodide (CH3ICH_3I) and the corresponding alcohol (ROHR-OH). This does not yield methyl alcohol.
  2. Exception (SN1): If one of the alkyl groups is tertiary (e.g., tert-butyl), the reaction proceeds via an SN1 mechanism due to the stability of the tertiary carbocation .
  • Protonation: The ether oxygen is protonated.
  • Cleavage: The bond between the oxygen and the tertiary carbon breaks, forming a stable tertiary carbocation and methyl alcohol (CH3OHCH_3OH).
  • Substitution: The iodide ion then attacks the tertiary carbocation to form tert-butyl iodide.

Therefore, only an ether with a tertiary group, like tert-butyl methyl ether ((CH3)3COCH3(CH_3)_3C-O-CH_3), will yield methyl alcohol (CH3OHCH_3OH) and the tertiary alkyl iodide.

Exam Context & Concepts Covered

This question aligns with the NEET CHEMISTRY syllabus, specifically targeting concepts from Alcohols, Phenols and Ethers. Mastering this topic is crucial for scoring well in the upcoming medical entrance examinations. Solving conceptually related problems will help you understand the nuances of these concepts and improve your problem-solving speed.

CHEMISTRYAlcohols, Phenols and Ethersfollowingethersproducemethylalcohol

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