Reaction of the compound corresponding to spectrum E with SOCl 2 produces a chloroalkane, C 4 H

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Reaction of the compound corresponding to spectrum E with SOCl2 produces a chloroalkane, C4H7Cl, whose NMR spectrum is almost identical with spectrum E, except that the broad signal at δ = 1.5 ppm is absent. Its IR spectrum shows bands at 700, 925, 985, 1640, and 3090 cm-1. Treatment with H2 over PtO2 results in C4H9Cl. Its IR spectrum reveals the absence of all the bands quoted for its precursor, except for the signal at 700 cm-1. Identify these two molecules.

1Η ΝMR 3 H 6.00 5.95 5.90 5.85 5.80 1 H1H 1 H 1 H 1 H (CH3)4Si 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.0 300-MHz 'H NMR spectrum ppm (8) E




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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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