(a) 3-Phenylpropanoyl chloride, C 6 H 5 CH 2 CH 2 COCl, reacts with AlCl 3 to...

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(a) 3-Phenylpropanoyl chloride, C6H5CH2CH2COCl, reacts with AlCl3 to give a single product 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, 2 H), and 7.2 – 7.7 (m, 4 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) NaBH4, CH3CH2OH; (2) Conc. H2SO4, 100 8C; (3) H2, Pd – C, CH3CH2OH. The final product exhibits five resonance lines in its 13C NMR spectrum. What is the structure of the substance formed after each of the steps in this sequence?

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Organic Chemistry structure and function

ISBN: 978-1429204941

6th edition

Authors: K. Peter C. Vollhardt, Neil E. Schore

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