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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Identify the structure and assign peaks and J values for an organic compound C4H3O with p-NMR (CDCI3, 400 MHz, 300 K) values at 8=1.01 (t), 1.56 (m), 2.47 (m), 3JHH =2.7 Hz, 3JHH =4.0 Hz. 2.73 (m), 2.88 (m).
Please give the correct answer to the following NMR spectroscopy question and provide detailed solutions of the answer.
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?

Chapter 14 Solutions

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