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3-Phenylpropanoyl chloride (C6H5CH2CH2COCl) reacts with AlCl3 to give a single product A with the formula C9H8O...

3-Phenylpropanoyl chloride (C6H5CH2CH2COCl) reacts with AlCl3 to give a single product A with the formula C9H8O and an 1H NMR spectrum with signals at δ = 2.53 (t, J = 8 Hz, 2 H), 3.02 (t, J = 8 Hz, 2H) and 7.2-7.7 (m, 4H) ppm. Propose a structure for this compound.

The product of the process described above is subjected to the following reaction sequence (1) NaBH4, EtOH; (2) conc. H2SO4,100 °C; (3) H2, Pd/C, EtOH. The resulting molecule exhibits five resonance lines in its 13C NMR spectrum. What is the structure of the substance formed after each of the steps in the sequence?

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3-Phenylpropanoyl chloride (C6H5CH2CH2COCl) reacts with AlCl3 to give a single product A with the formula C9H8O...
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