Organic Chemistry 2 - 14.16

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Organic Chemistry 2 - 14.16

Problem 14.16
bato
How many signals would you expect to see in the ¹³C NMR spectrum of each of the following
compounds?
(a) Propylbenzene
(b) Isopropylbenzene
(c) 1,2,3-Trimethylbenzene
mmotno bre AMM ET.AN
Sample Solution (a) The two ring carbons that are ortho to the propyl substituent are
equivalent and so must have the same chemical shift. Similarly, the two ring carbons that are
meta to the propyl group are equivalent to each other. The carbon atom para to the
substituent is unique, as is the carbon that bears the substituent. Thus, there will be four
signals for the ring carbons, designated w, x, y, and z in the structural formula. These four
signals for the ring carbons added to those for the three nonequivalent carbons of the
propyl group yield a total of seven signals.
W
X
y
x y
(d) 1,2,4-Trimethylbenzene
(e) 1,3,5-Trimethylbenzene
Z
CH₂CH2CH3
Transcribed Image Text:Problem 14.16 bato How many signals would you expect to see in the ¹³C NMR spectrum of each of the following compounds? (a) Propylbenzene (b) Isopropylbenzene (c) 1,2,3-Trimethylbenzene mmotno bre AMM ET.AN Sample Solution (a) The two ring carbons that are ortho to the propyl substituent are equivalent and so must have the same chemical shift. Similarly, the two ring carbons that are meta to the propyl group are equivalent to each other. The carbon atom para to the substituent is unique, as is the carbon that bears the substituent. Thus, there will be four signals for the ring carbons, designated w, x, y, and z in the structural formula. These four signals for the ring carbons added to those for the three nonequivalent carbons of the propyl group yield a total of seven signals. W X y x y (d) 1,2,4-Trimethylbenzene (e) 1,3,5-Trimethylbenzene Z CH₂CH2CH3
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