An unknown aromatic compound, P, has the molecular formula C_13H_16. Compound P

Question

An unknown aromatic compound, P, has the molecular formula C_13H_16. Compound P reacts with Br_2/CCl_4 to give a tetrabrominated compound, C_13H_16Br_4. When compound P is treated with hot, basic permanganate solution followed by acid, three different molecules, Q, R, and S, are produced. Compound Q is identical to the product obtained by the side-chain oxidation of meta-xylene. Compound R, C_3H_6O, has only a single peak absorbance in its nmr spectrum. Compound S, C_2H_4O_2, is water-soluble. Draw structures for compounds P, Q, R, and S. Outline a synthesis for each of the following compounds. You may start with benzene or aniline and any other compound containing not more than three carbon atoms. Show all reaction steps, reagents, and conditions.

Explanation / Answer

9. Drawn below are the structures for P, Q, R and S from the given analysis data

10. The detailed synthetic schemes with all the reagents are given below.

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