From the following information, deduce the structure of coniine, a toxic amine found in poison hemlock, which,

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From the following information, deduce the structure of coniine, a toxic amine found in poison hemlock, which, deservedly, has a very bad reputation. IR: 3330 cm-1. 1H NMR: δ = 0.91 (t, J = 7 Hz, 3 H), 1.33 (s, 1 H), 1.52 (m, 10 H), 2.70 (t, J = 6 Hz, 2 H), and 3.0 (m, 1 H) ppm. Mass spectrum: m/z (relative intensity) = 127 (M+, 43), 84(100), and 56(20). 

1. CH;I 2. Ag,0, H,0 3. A 1. CH;I 2. Ag.0, H,O 3. A mixture of mixture of Coniine three compounds (CH3)3N + 1,4-octadiene and 1,5-octadiene

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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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