Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 14, Problem 14PP

Practice Problem 14.14

Explain how 13 C NMR spectroscopy could be used to distinguish the ortho-, meta-, and para-dibromobenzene isomers one from another.

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Compound A with molecular formula C6H10 has two peaks in its 1H NMR spectrum, both of which are singlets (with ratio 9 : 1). Compound A reacts with an acidic aqueous solution containing mercuric sulfate to form compound B, which gives a positive iodoform test and has an 1H NMR spectrum that shows two singlets (with ratio 3 : 1). Identify A and B.
Propose a structure of compound C (molecular formula C10H12O) consistent with the following data. C is partly responsible for the odor and flavor of raspberries. Compound C: IR absorption at 1717 cm-1
1. Predict the maximum total number of possible peaks in the 13C NMR spectrum of sesamin (Hint: , keep in mind the molecule’s symmetry when predicting the # of NMR peaks) a. Indicate the number of non-aromatic peaks in the 13C NMR of sesamin b.Indicate the number of aromatic peaks in the 13C NMR of sesamin

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NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY