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NEET CHEMISTRYMedium

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.

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