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 15PP

PRACTICE PROBLEM 14.15

Four benzenoid compounds, all with the formula C 7 H 7 Br , gave the following IR peaks in the 680–860 cm 1 region:

A, 740 cm 1 (strong)

B, 800 cm 1 (very strong)

C, 680 cm 1 (strong) and 760 cm 1 (very strong)

D, 693 cm 1 (very strong) and 765 cm 1 (very strong)

Propose structures for A, B, C, and D.

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9. (a) A compound with chemical formula C₂H₂CIBr shows the proton NMR spectrum consisting of two doublets with J-7.3 Hz. What is the molecular structure of this compound? (b) The proton chemical shifts of the two doublets from the previous question differ by 0.3 ppm. Can you consider the proton spectrum as the first order one?
Consider the aromatic compound 4-isopropyl-benzonitrile. (Benzonitrile is a benzene ring with the nitrile group on position 1.)   How many signals for non-equivalent types of protons will be in its proton NMR spectrum?
Define the 1H NMR spectrum of 2-bromopropane, (CH3)2CHBr

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