Compound A has molecular formula C8H8O. An IR spectrum of compound A exhibits a signal

Chapter 19, Problem 19.74

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Compound A has molecular formula C8H8O. An IR spectrum of compound A exhibits a signal at 1680 cm-1 . The 1 H NMR spectrum of compound A exhibits a group of signals between 7.5 and 8 ppm (with a combined integration of 5) and one upfield signal with an integration of 3. Compound A is converted into compound B under the following conditions: Compound A Compound B Zn(Hg), HCl, heat When compound B is treated with Br2 and AlBr3, two different monobromination products are obtained. Identify both of these products and predict which one will be the major product. Explain your reasoning.

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