Q23 / 192 · NTA Abhyas (NEET) 2020 · Chemistry · Alcohols Phenols and Ethers

Among the following ethers, which one will produce methyl alcohol on treatment with hot concentrated HI?

  • A
    CH3-CH2-CH(CH3)-O-CH3
  • Correct answer
    B
    (CH3)3C-O-CH3
  • C
    (CH3)2CH-CH2-O-CH3
  • D
    CH3-CH2-CH2-CH2-O-CH3

Solution

Figure
In in this reaction a stable tertiary carbocation is possible so SN1 mechanism is used and I- in SN1 is taken with stable carbocation.
In rest other options SN2 mechanism will be used as stable carbocations are not possible hence I- goes with CH3 group to give CH3I and respective alcohols.

Hence, the correct answer is option: 'B'.

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