Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 13.12F, Problem 13.28P
Interpretation Introduction
Interpretation: The DEPT-90 and DEPT-135 spectra for the given
Concept introduction: NMR spectroscopy is a technique used to determine a unique structure of the compounds. It identifies the carbon-hydrogen bonding of an organic compound. A hydrogen atom is called as a proton in the NMR spectroscopy.
To determine: The DEPT-90 and DEPT-135 spectra for the given
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4. Below are the IR regions and NMR chemical shifts table for use with the spectroscopy problems:
'H NMR
12 11
R
20
ΟΞΟ
10
OH R
0=C
H
9 8
7
ppm
6
OH
H C=C-H
5
NH
H-C-X
H-C-O
-OH
X = F, Cl, Br
(i.e. electronegative atom)
3
-NH
2
H-C-N
H-C-S
HC-
1
-CH3
-CH₂-
CEC-H
H-C-C=O -CH
H-C-C=C
0
4000
DID
small range
range of values
broad peak
=C-H
⇓
3250-
3300
N-H
broad with spikes
-3300
-O-H
broad-3300
-3400
3500
-O-H -CEN
N-H CO
I, I
=C
H
2730-
2820
道
H
3000- 2 peaks
3100
-C-H
2850-
2960
0
-C-O-H
broad-3000
3000
usually
strong
-CEN
B
2200
-CICH
3
2200
2500
wavenumber, cm-¹
2000
C
C
HC N
1680
OR
1730
200
C.
H
1600-
1660
0.585
1710
C.
NA₂
1650
3
1600
O
1500
***
1000
These are four alcohols with the formula C4H10O. One of them produced this C-NMR spectrum, which alcohol did that and what carbons correspond with what peaks?
Two bottles labelled cis-cyclohexandiol were found in a
laboratory. Because of their differing melting points, the
bottles clearly contained two different cis-cyclohexandiol
isomers. To determine which isomer was in which bottle,
the chemist decided to run ¹3C NMR spectra on a
sample of each. The three possible products were as in
the figure. (Figure 1)
The two ¹³C NMR proton-decoupled spectra contained
the following data:
●
●
Figure
HO
spectrum of sample in bottle A: 20.20,
62.55
spectrum of sample in bottle B: 16.09,
29.52, 36.15, 63.08
OH
OH
OH
1 of 1
OH
OH
Part A
Identify which isomer was present in the bottle A.
OH
HO
OH
OH
OH
OH
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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