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Consider the following reaction sequence: Cumene undergoes (i) O2/air/heat, then (ii) H3O+ to give aromatic product X. Product X then undergoes (i) NaOH/CO2, then (ii) acetic anhydride/H+ to give aromatic product Y. How many oxygen atoms are present in one molecule of Y?
- 1
- 2
- 3
- 4
Correct answer: 4
Solution
Cumene -> cumene hydroperoxide -> (acid) phenol (X). Phenol -> (Kolbe) salicylic acid -> (Ac2O/H+) aspirin = 2-(acetyloxy)benzoic acid, C9H8O4, with 4 oxygen atoms.
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