Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Question
Chapter 4.7, Problem 16P
Interpretation Introduction
Interpretation:
The reason for not having any steric strain in axial cyanosubstituted cyclohexane is to be explained with the help of molecular model.
Concept introduction:
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2. Predict the NMR spectra for each of these two
compounds by listing, in the NMR tables below, the
chemical shift, the splitting, and the number of
hydrogens associated with each predicted peak. Sort the
peaks from largest chemical shift to lowest.
**Not all slots must be filled**
Peak
Chemical Shift (d)
5.7
1
Multiplicity
multiplate
..........
5.04
double of doublet
2
4.98
double of doublet
3
4.05
doublet of quartet
4
5
LO
3.80
quartet
1.3
doublet
6
Peak
Chemical Shift (d)
Multiplicity
Interpreting NMR spectra is a skill that often requires some
amount of practice, which, in turn, necessitates access to a
collection of NMR spectra. Beyond Labz Organic Synthesis and
Organic Qualitative Analysis have spectral libraries containing
over 700 1H NMR spectra. In this assignment, you will take
advantage of this by first predicting the NMR spectra for two
closely related compounds and then checking your predictions
by looking up the actual spectra in the spectra library. After
completing this assignment, you may wish to select other
compounds for additional practice.
1. Write the IUPAC names for the following two structures:
Question 2
Question 3
2. Predict the NMR spectra for each of these two
compounds by listing, in the NMR tables below, the
chemical shift, the splitting, and the number of
hydrogens associated with each predicted peak. Sort the
peaks from largest chemical shift to lowest.
**Not all slots must be filled**
11:14
...
worksheets.beyondlabz.com
3. To check your predictions, click this link for Interpreting
NMR Spectra 1. You will see a list of all the
-
compounds in the spectra library in alphabetical order by
IUPAC name. Hovering over a name in the list will show
the structure on the chalkboard. The four buttons on the
top of the Spectra tab in the tray are used to select the
different spectroscopic techniques for the selected
compound. Make sure the NMR button has been selected.
4. Scroll through the list of names to find the names for the
two compounds you have been given and click on the
name to display the NMR spectrum for each. In the NMR
tables below, list the chemical shift, the splitting, and
the number of hydrogens associated with each peak for
each compound. Compare your answers to your
predictions.
**Not all slots must be filled**
Peak
Chemical Shift (d)
Multiplicity
1
2
3
4
5
Chapter 4 Solutions
Organic Chemistry
Ch. 4.1 - Give IUPAC names for the following cycloalkanes:Ch. 4.1 - Draw structures corresponding to the following...Ch. 4.1 - Name the following cycloalkane:Ch. 4.2 - Prob. 4PCh. 4.2 - Draw the structures of the following molecules:...Ch. 4.2 - Prostaglandin F2α, a hormone that causes uterine...Ch. 4.2 - Name the following substances, including the cis-...Ch. 4.3 - Each H↔H eclipsing interaction in ethane costs...Ch. 4.3 - cis-1, 2-Dimethylcyclopropane has more strain than...Ch. 4.4 - Prob. 10P
Ch. 4.4 - Two conformations of cis-l, 3-dimethylcyclobutane...Ch. 4.6 - Draw two different chair conformations of...Ch. 4.6 - Draw two differant chair conformations of trans-1,...Ch. 4.6 - Prob. 14PCh. 4.7 - What is the energy difference between the axial...Ch. 4.7 - Prob. 16PCh. 4.7 - Look at Figure 4-12 on page 105, and estimate the...Ch. 4.8 - Draw the more stable chair conformation of the...Ch. 4.8 - Identify each substituent in the following...Ch. 4.9 - Which isomer is more stable, cis-decalin or...Ch. 4.9 - Look at the following structure of the female...Ch. 4.SE - Prob. 22VCCh. 4.SE - Name the following compound, identify each...Ch. 4.SE - A trisubstituted cyclohexane with three...Ch. 4.SE - The following cyclohexane derivative has three...Ch. 4.SE - Prob. 26VCCh. 4.SE - Draw the five cycloalkanes with the formula C5H10.Ch. 4.SE - Draw two constitutional isomers of cis-1,...Ch. 4.SE - Prob. 29APCh. 4.SE - Tell whether the following pairs of compounds are...Ch. 4.SE - Prob. 31APCh. 4.SE - Prob. 32APCh. 4.SE - Draw 1, 3, 5-trimethylcyclohexane using a hexagon...Ch. 4.SE - Hydrocortisone, a naturally occurring hormone...Ch. 4.SE - A 1, 2-cis disubstituted cyclohexane, such as...Ch. 4.SE - A 1, 2-trans disubstituted cyclohexane must have...Ch. 4.SE - Prob. 37APCh. 4.SE - Which is more stable, a 1, 4-trans disubstituted...Ch. 4.SE - cis-1, 2-Dimethylcyclobutane is less stable than...Ch. 4.SE - From the data in Figure 4-12 and Table 4-1,...Ch. 4.SE - Prob. 41APCh. 4.SE - Draw the two chair conformations of...Ch. 4.SE - Draw the two chair conformations of...Ch. 4.SE - Galactose, a sugar related to glucose, contains a...Ch. 4.SE - There are four cis-trans isomers of menthol...Ch. 4.SE - There are four cis-trans isomers of menthol...Ch. 4.SE - The diaxial conformation of cis-1,...Ch. 4.SE - Approximately how much steric strain does the...Ch. 4.SE - In light of your answer to Problem 4-43, draw the...Ch. 4.SE - Prob. 50APCh. 4.SE - Prob. 51APCh. 4.SE - Using molecular models as well as structural...Ch. 4.SE - trans-Decalin is more stable than its cis isomer,...Ch. 4.SE - As mentioned in Problem 3-53, the statin drugs,...Ch. 4.SE - myo-Inositol, one of the isomers of...Ch. 4.SE - How many cis–trans stereoisomers of myo-inositol...Ch. 4.SE - The German chemist J. Bredt proposed in 1935 that...Ch. 4.SE - Tell whether each of the following substituents on...Ch. 4.SE - Prob. 59APCh. 4.SE - Prob. 60APCh. 4.SE - Ketones react with alcohols to yield products...Ch. 4.SE - Alcohols undergo an oxidation reaction to yield...
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