(a) 3-Phenylpropanoyl chloride, \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2}
\mathrm{CH}_{2} \mathrm{COCl}\), reacts with \(\mathrm{AlCl}_{3}\) to give a
single product with the formula \(\mathrm{C}_{9} \mathrm{H}_{8} \mathrm{O}\) and
an \({ }^{1} \mathrm{H}\) NMR spectrum with signals at \(\delta=2.53(\mathrm{t},
J=8 \mathrm{~Hz}, 2 \mathrm{H})\), \(3.02(\mathrm{t}, J=8 \mathrm{~Hz}, 2
\mathrm{H})\), and \(7.2-7.7(\mathrm{~m}, 4 \mathrm{H})\) ppm. Propose a
structure and a mechanism for the formation of this product.
(b) The product of the process described in (a) is subjected to the following
reaction sequence:
(1) \(\mathrm{NaBH}_{4}, \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH} ;\) (2)
Conc. \(\mathrm{H}_{2} \mathrm{SO}_{4}, 100^{\circ} \mathrm{C} ;\) (3)
\(\mathrm{H}_{2}, \mathrm{Pd}-\mathrm{C}, \mathrm{CH}_{3} \mathrm{CH}_{2}
\mathrm{OH}\). The final product
exhibits five resonance lines in its \({ }^{13} \mathrm{C}\) NMR spectrum. What
is the structure of the substance formed after each of the steps in this
sequence?