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The major product in the given reaction sequence is Q. The mass spectrum of Q shows

([M] = molecular ion peak)

Phenol treated with 1. NaOH, CO2, then H3O+ and 2. Br2 - water (excess), giving Q

  • A.[M], [M+2], [M+4], and [M+6] peaks with relative intensity of 1:1:1:1
  • B.[M], [M+2], [M+4], and [M+6] peaks with relative intensity of 1:3:3:1
  • C.[M], [M+2], and [M+4] peaks with relative intensity of 1:2:1
  • D.[M] and [M+2] peaks with relative intensity of 1:1

Answer: B

Q shows [M], [M+2], [M+4] and [M+6] peaks in the ratio 1:3:3:1.

Step 1 is the Kolbe-Schmitt reaction: sodium phenoxide and CO2 give salicylic acid after acidification. In step 2, excess bromine water brominates both positions ortho and para to the strongly activating OH and displaces the carboxyl group (bromodecarboxylation), so Q is 2,4,6-tribromophenol.

Bromine's isotopes 79Br and 81Br are almost equally abundant, so a molecule with three bromines gives a binomial pattern \((1 + 1)^{3}\): peaks at M, M+2, M+4 and M+6 in the ratio 1:3:3:1. One bromine gives 1:1 and two give 1:2:1, the patterns of the other options; 1:1:1:1 matches no isotope distribution.

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