Myosmine can be isolated from tobacco, along with several other structurally similar
Chapter 15, Problem 15.76(choose chapter or problem)
Myosmine can be isolated from tobacco, along with several other structurally similar compounds, including nicotine. The originally accepted structure for myosmine was disproven with IR spectroscopy (Anal. Chem. 1954, 26, 14281431): N N Originally accepted H structure of myosmine :DYHQXPEHU FP 7UDQVPLWWDQFH (a) Explain why the IR spectrum is not consistent with the originally proposed structure. (b) The discord between the proposed structure and its IR spectrum was resolved by recognizing that myosmine exists primarily as a tautomer of the proposed structure. Draw this tautomer and explain why its structure is more consistent with the observed IR spectrum. (c) Identify a likely source for the fairly intense signal at 1621 cm-1 .
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