Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 13.12E, Problem 13.26P
- a. Show which carbon atoms correspond with which peaks in the 13 C N M R spectrum of butan-2-one (Figure 13-45).
- b. Draw the proton NMR spectrum you would expect lor butan-2-one. How well do the proton chemical shifts predict the carbon chemical shifts using the “15 to 20 times as large” rule of thumb?
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a. Rank the indicated protons in increasing order of chemical shift. Fill in the boxes with
the correspondants letters to the indicated hydrogens.
b. Explain your choice of chemical shifts order for protons He and Hd.
Hc
Ha
Ha
He
< SH
< δΗ
8 H
< SH
Hb
< SH
1. Which proton has the largest multiplicity? Smallest multiplicity?
Ha
Hd.
Hb
2. Which proton has the largest chemical shift? Smallest chemical shift?
He
Hc
Hf
'H-NMR exercises
A. Number of signals, integration, and multiplicity
1. Determine the number of signals, the integration per signal, and the multiplicity of each
signal for the 1H-NMR spectrum of the following molecule
B. Chemical Displacement
1. With the chemical shift table determine what type
of proton are the protons H., He and He ( >:
C. Unknown C,H20
1. Complete the table below, indicating in the corresponding spaces.
Sign
2. Using the same structure, place in descending order of chemical shift (highest
to lowest) of the protons H., Ho, and He():
->__
A
B
C
188
chemical
shift
7.2
35
2
C₂H12O
Integration
PPM
112
76
unfolding
Hal
75
3
multiplete
ho
C-CEC-H₂
Proton Type
Chapter 13 Solutions
Organic Chemistry (9th Edition)
Ch. 13.5A - In a 300-MHz spectrometer, the protons in...Ch. 13.5B - Prob. 13.2PCh. 13.6 - Determine the number of different kinds of protons...Ch. 13.6 - Prob. 13.4PCh. 13.7 - Draw the integral trace expected for the NMR...Ch. 13.7 - Prob. 13.6PCh. 13.8C - Draw the NMR spectra you would expect for the...Ch. 13.8D - Draw the NMR spectra you expect for the following...Ch. 13.8D - a. Assign protons to the peaks in the NMR spectrum...Ch. 13.8D - Prob. 13.10P
Ch. 13.8D - Two spectra are shown. Propose a structure that...Ch. 13.9 - Prob. 13.12PCh. 13.9 - The spectrum of trans-hex-2-enoic acid follows. a....Ch. 13.9 - Prob. 13.14PCh. 13.9 - Prob. 13.15PCh. 13.10 - Prob. 13.16PCh. 13.10 - If the imaginary replacement of either of two...Ch. 13.10 - Predict the theoretical number of different NMR...Ch. 13.11B - Prob. 13.19PCh. 13.11B - Prob. 13.20PCh. 13.11B - Prob. 13.21PCh. 13.11B - Prob. 13.22PCh. 13.11B - Prob. 13.23PCh. 13.11B - Prob. 13.24PCh. 13.12E - Draw the expected broadband-decoupled 13 C N M R...Ch. 13.12E - a. Show which carbon atoms correspond with which...Ch. 13.12E - Repeat Problem13-25, sketching the...Ch. 13.12F - Prob. 13.28PCh. 13.13 - A bottle of allyl bromide was found to contain a...Ch. 13.13 - A laboratory student was converting cyclohexanol...Ch. 13.14 - Sets of spectra are given for two compounds. For...Ch. 13 - An unknown compound has the molecular formula C 9...Ch. 13 - Prob. 13.34SPCh. 13 - Predict the approximate chemical shifts of the...Ch. 13 - Prob. 13.36SPCh. 13 - Prob. 13.37SPCh. 13 - Prob. 13.38SPCh. 13 - Prob. 13.39SPCh. 13 - Prob. 13.40SPCh. 13 - For each compound shown below. 1. sketch the 13 C...Ch. 13 - Prob. 13.42SPCh. 13 - Prob. 13.43SPCh. 13 - Prob. 13.44SPCh. 13 - Prob. 13.45SPCh. 13 - Prob. 13.46SPCh. 13 - A compound was isolated as a minor constituent in...Ch. 13 - Prob. 13.48SPCh. 13 - The three isomers of dimethylbenzene are commonly...Ch. 13 - a. Draw all six isomers of formula C 4 H 8...Ch. 13 - Prob. 13.51SPCh. 13 - Hexamethylbenzene undergoes free-radical...Ch. 13 - Each of these four structures has molecular...Ch. 13 - Prob. 13.54SPCh. 13 - Phenyl Grignard reagent adds to 2-methylpropanal...Ch. 13 - Prob. 13.56SP
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