Q2 / 75 · JEE Main 2020 (02 Sep Shift 2) · Chemistry

An organic compound 'A' C9H10O when treated with conc. HI undergoes cleavage to yield compound 'B' and 'C'. 'B' gives yellow precipitate with AgNO3 where as 'C' tautomerizes to 'D'. 'D' gives positive iodoform test. 'A' could be:

  • A
    Figure
  • B
    Figure
  • Correct answer
    C
    Figure
  • D
    Figure

Solution

Benzene ring should not be attached to O atom otherwise it will yield phenol after reacting withHI so third option is prefect which gives benzyl iodide and it gives yellow precipitate of AgI after reacting with AgNO3. Another product tautomerises and gives acetaldehyde which gives iodoform test.

Figure

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

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