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m-eresol product p-cresel product In this example of the dienone-phenol rearrangement, this naphthalenic dienone is treated with aqueous acid to yield both m-cresol and p-cresol

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m-eresol product p-cresel product In this example of the dienone-phenol rearrangement, this naphthalenic dienone is treated with aqueous acid to yield both m-cresol and p-cresol products, depending upon how the rearrangement occurs. The mechanism for the generation of the m-cresol product involves the following steps: 1. Protonation of the carbonyl to yield product A; 2. A 1,2-methyl shift to yield carbocation 2; 3. Deprotonation to form the final aromatic product. The mechanism leading to the p-cresol product involves the foliowing steps: 1. Protonation of the carbonyl to yield product A; 2. An alkyl shift leading to spirocyclic intermediate 2; 3. A second alkyl shift leading to the formation of fused ring 3; 4. Deprotonation to form the final aromatic product. For the formation of the p-cresol product, write out the mechanism on a separate sheet of paper and then draw the structure of spirocyclic intermediate 2 in th window below. Treatment of gamma-pyran with the hydride (H)acceptor triphenylmethyl perchlorate gives triphenylmethane and the perchlorate sait A,C5H5ClO5. Draw the cation of A as its most stable resonance form. (C6H5)3C+ClO4 AC5H5ClO5+(C6H5)3CH y ypyran - Draw cations and anions in separate sketchers. - Separate structures with + signs from the drop-down menu. - Omit the perchlorate lon

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