Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 13, Problem 13.50SP
- a. Draw all six isomers of formula C 4 H 8 (including stereoisomers).
- b. For each structure, show how many types of H would appear in the proton NMR spectrum.
- c. For each structure, show how many types of C would appear in the 13 C N M R spectrum.
- d. If an unknown compound of formula C 4 H 8 shows two types of H and three types of C, can you determine its structure from this information?
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I need help interpreting these 3 spectra, h-nmr,c-nmr, IR. All three correlate to same molecular structure. The question asks you to determine the molecular structure and label all peaks on all 3 spectra.
Connections to biology
5. Tyrosine is an important amino acid in Biochemistry. Assign the peaks in the ¹H-NMR to the hydrogens
in the structure of tyrosine by placing a, b, c, and d in the appropriate corresponding boxes. The
hydrogen atoms attached to O and N atoms do not need to be labeled on this spectrum.
b
14
12
10
d
HN
C
NH₂
histidine
PPM
OH
Propose a structure for the following NMR spectra of a compound with chemical formula
C8H9BR. Draw your final structure in the box. Assign all peaks to atoms in your structure.
Chem.
shift
Rel.
area
1.20
3.00
2.58
2.00
7.07
2.00
7.39
2.00
TMS
10
9.
8.
7
6.
4
1
0 ppm
Chemical shift (8)
TMS
80
60
40
0 ppm
160
140
120
100
200
180
Chemical shift (8)
20
2.
3.
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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