(a) 3-Phenylpropanoyl chloride, C6H5CH2CH2COCl, reacts with AlCl3 to give a single
Chapter 15, Problem 53(choose chapter or problem)
(a) 3-Phenylpropanoyl chloride, C6H5CH2CH2COCl, reacts with AlCl3 to give a single productwith the formula C9H8O and an 1H NMR spectrum with signals at d 5 2.53 (t, J 5 8 Hz, 2 H),3.02 (t, J 5 8 Hz, 2 H), and 7.2 7.7 (m, 4 H) ppm. Propose a structure and a mechanism forthe formation of this product.(b) The product of the process described in (a) is subjected to the following reaction sequence:(1) NaBH4, CH3CH2OH; (2) Conc. H2SO4, 100 8C; (3) H2, Pd C, CH3CH2OH. The fi nal productexhibits fi ve resonance lines in its 13C NMR spectrum. What is the structure of the substanceformed after each of the steps in this sequence?
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