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 9PP

Practice Problem 14.9

In 1967 R. Breslow (of Columbia University) and co-workers showed that adding S b C l 5 to a solution of 3-chlorocyclopropene in C H 2 C l 2 caused the precipitation of a white solid with the composition C 3 H 3 + S b C l 6 . NMR spectroscopy of a solution of this salt showed that all of its hydrogen atoms were equivalent.

(a) What new aromatic ion had these researchers prepared?

(b) How many 13 C NMR signals would you predict for this ion?

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