
Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 8, Problem 51P
Interpretation Introduction
Interpretation:
Three different sets of reagents that can be used to synthesize the alkylbenzyldimethylammonium chloride have to be shown.
Concept Introduction:
Alkylbenzyldimethylammonium chloride is on leave-on skin antiseptic used to treat such things cuts and cold sores. It is also the antiseptic in many hand sanitizers. It is actually a mixture of compounds that differ in the number of carbons (any even number between 8 and 18) in the alkyl group.
In a quaternary ammonium ion a nitrogen atom with four attached groups is positively charged. And their compounds are known as quaternary ammonium salt.
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5 (a). Using the peak information you listed in the tables for
both structures, assign each peak to that portion of the
structure that produces the peak in the NMR spectrum. Draw
this diagram on your own sheet of paper and attach the sketch
of your drawing to this question.
Question 6
5 (b). Using the peak information you listed in the tables for
both structures, assign each peak to that portion of the
structure that produces the peak in the NMR spectrum. Draw
this diagram on your own sheet of paper and attach the sketch
of your drawing to this question.
Question 7
6. Are there any differences between the spectra you obtained
in Beyond Labz and the predicted spectra? If so, what were
the differences?
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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**
Chapter 8 Solutions
Essential Organic Chemistry (3rd Edition)
Ch. 8.1 - Prob. 2PCh. 8.1 - Does increasing the energy barrier for an SN2...Ch. 8.1 - Arrange the following alkyl bromides in order from...Ch. 8.2 - Prob. 7PCh. 8.2 - Which reaction in each of the following pairs...Ch. 8.2 - Prob. 9PCh. 8.2 - Prob. 11PCh. 8.3 - Draw the substitution products that will be formed...Ch. 8.4 - Arrange the following alkyl halides in order from...Ch. 8.5 - Prob. 14P
Ch. 8.5 - Which of the following reactions will go faster if...Ch. 8.6 - After a proton is removed from the OH group, which...Ch. 8.6 - Draw the product of each of the following...Ch. 8.9 - Prob. 20PCh. 8.9 - Prob. 21PCh. 8.11 - Why do the SN1/E1 reactions of tertiary alkyl...Ch. 8.11 - Prob. 23PCh. 8.11 - Prob. 24PCh. 8.12 - Prob. 25PCh. 8.12 - Prob. 26PCh. 8.12 - Prob. 27PCh. 8.12 - a In which solvent would tert-butyl bromide...Ch. 8.13 - What would be the best way to prepare the...Ch. 8 - Methoxychlor is an insecticide that was intended...Ch. 8 - Prob. 31PCh. 8 - Prob. 32PCh. 8 - Prob. 33PCh. 8 - Prob. 34PCh. 8 - Prob. 35PCh. 8 - Prob. 36PCh. 8 - Explain how the following changes would affect the...Ch. 8 - Prob. 38PCh. 8 - Draw the major product obtained when each of the...Ch. 8 - Which alkyl halide in Problem 39 can undergo an El...Ch. 8 - Prob. 42PCh. 8 - Prob. 43PCh. 8 - Prob. 44PCh. 8 - Prob. 45PCh. 8 - Starting with bromocyclohexane, how could the...Ch. 8 - Prob. 48PCh. 8 - Fill in the blanks in the following chemical...Ch. 8 - For each of the following alkyl halides, indicate...Ch. 8 - Prob. 51PCh. 8 - a. Explain why 1-bromo-2,2-dimethylpropane has...Ch. 8 - An ether can be prepared by an SN2 reaction of an...Ch. 8 - Give two sets of reactants (each set including an...Ch. 8 - Show how the following compounds could be...Ch. 8 - Prob. 56PCh. 8 - Prob. 57PCh. 8 - Draw the structures of the products obtained from...Ch. 8 - cis-4-Bromocyclohexanol and...Ch. 8 - Prob. 60PCh. 8 - Prob. 61PCh. 8 - Prob. 62PCh. 8 - Prob. 63PCh. 8 - In which solventethanol or diethyl etherwould the...Ch. 8 - The pKa of acetic acid in water is 4.76. What...
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- 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 5arrow_forwardО δα HO- H -Br δα HO-- + + -Br [B] 8+ HO- -Br δα नarrow_forward1/2 - 51% + » GAY Organic Reactions Assignment /26 Write the type of reaction that is occurring on the line provided then complete the reaction. Only include the major products and any byproducts (e.g. H₂O) but no minor products. Please use either full structural diagrams or the combination method shown in the lesson. Skeletal/line diagrams will not be accepted. H3C 1. 2. CH3 A Acid OH Type of Reaction: NH Type of Reaction: + H₂O Catalyst + HBr 3. Type of Reaction: H3C 4. Type Reaction: 5. H3C CH2 + H2O OH + [0] CH3 Type of Reaction: 6. OH CH3 HO CH3 + Type of Reaction: 7. Type of Reaction: + [H]arrow_forward
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