MCPHS Organic Chemistry Dehydration of Alcohol to Form Alkenes Lab Report

5-4: Alcohol DehydrationFor this assignment, the target compound that you should synthesize is cyclohexene. This is an
elimination react. Assess the potential of the possible leaving groups. Keep in mind the mechanism and
how that controls the outcome of the process.
Synthesis Procedures
1. Start Virtual ChemLab and select Alcohol Dehydration from the list of assignments on the
whiteboard. After entering the synthesis laboratory, Use the available reagents on the stockroom shelf
and identify the appropriate starting materials required to synthesize the target compound and add
them to the round bottom flask. Select the appropriate solvent and drag the flask to the Stir Plate on
the lab bench.
2. The round bottom flask containing the starting materials should now be on the stir plate, and the
contents of the flask should be visible on the chalkboard. From the group of reagents found on the lab
bench, select the correct reagent to synthesize the target compound and add it to the flask on the stir
plate.
3. Start the reaction by clicking on the Stir button on the front of the stir plate. You should be able to
observe the reaction mixture stirring in the flask. Monitor the progress of the reaction using TLC
measurements as necessary until the product has formed and the starting materials have been
consumed. You can advance the laboratory time using the clock on the wall. With the electronic lab
book open (click on the lab book on the stockroom counter), you can also save your TLC plates by
clicking Save on the TLC window.
4. When the reaction is complete, “work up” your reaction by first dragging and dropping the separatory
funnel on the flask and then adding H2O the funnel. Extract the organic layer in the funnel by clicking
on the top layer and dragging it to the cork ring on the lab bench. Your target compound should now
be in this flask.
List the starting materials, solvent, reagent, and products formed:
How long did it take to finish the reaction?
What are the TLC values (Rf) for (a) Starting Materials:
(b) Products:
Write a mechanism for this reaction:
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FTIR and NMR Spectra
After completing a reaction and working up the products, it is still necessary to confirm that the correct
product was formed. The most common tools used for this analysis are Fourier Transform Infrared (FTIR)
and Nuclear Magnetic Resonance (NMR) spectroscopy. In the virtual laboratory, 1H and 13C NMR
spectra are available. Details on interpreting FTIR and NMR spectra are found in your textbook. Your
instructor may or may not ask you to perform this section depending on how your class is structured.
5. To collect an FTIR spectrum of your product, click on the FTIR spectrometer located to the right of
the lab bench and drag the salt plate icon to the flask on the lab bench. A window containing the FTIR
spectrum for your product should now open. Identify the relevant peaks in the FTIR spectrum and
record the position and associated functional group for each in the FTIR table below. The FTIR
spectrum can also be saved to the lab book for later analysis.
FTIR
List position (cm-1) & functional group
4.
1.
5.
2.
6.
3.
7.
6. To collect a 1H NMR spectrum of your product, click on the NMR magnet located to the right of the
chalkboard and drag the NMR sample tube to the flask on the lab bench. A window containing the
NMR spectrum for your product should now open. You can zoom into various portions of the NMR
spectrum by clicking and dragging over the desired area. The Zoom Out button is used to zoom back
out to view the full spectrum. Identify all of the peaks in the NMR spectrum and record the chemical
shift, the splitting, and the number of hydrogens for each peak in the NMR table below. The NMR
spectrum can also be saved to the lab book for later analysis. If necessary to confirm the structure of
your product, you can measure the 13C NMR for the product and record the chemical shifts for the
peaks. Mass spectrometry is also available if needed.
1
H NMR
Structure:
Cyclohexene
†
‡
Peak
Chemical
Shift (δ)
Multiplicity†
H‡
Peak
1
7
2
8
3
9
4
10
5
11
6
12
Chemical
Shift (δ)
Multiplicity†
H‡
Specify the multiplicity as a singlet (s), doublet (d), triplet (t), quartet (q), or multiplet (m).
Specify the number of hydrogens associated with each peak.
7. Do the FTIR and NMR spectra you measured and recorded in the tables above confirm that you
synthesized the assigned target compound? Explain.
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12-1: Alcohol Oxidation – 1
For this assignment, the target compound that you should synthesize is benzoic acid. This is an oxidation
reaction. Examine the product and determine a lower oxidation state functional group that may be present
in the starting material.
Synthesis Procedures
1. Start Virtual ChemLab and select Alcohol Oxidation – 1 from the list of assignments on the
whiteboard. After entering the synthesis laboratory, use the available reagents on the stockroom shelf,
identify the appropriate starting materials required to synthesize the target compound and add them to
the round bottom flask. Select the appropriate solvent and drag the flask to the Stir Plate on the lab
bench.
2. The round bottom flask containing the starting materials should now be on the stir plate, and the
contents of the flask should be visible on the chalkboard. From the group of reagents found on the lab
bench, select the correct reagent to synthesize the target compound and add it to the flask on the stir
plate. Now attach the heater, condenser, and N2 gas to the round bottom flask so the reaction mixture
can be heated.
3. Start the reaction by clicking on the Stir button on the front of the stir plate. You should be able to
observe the reaction mixture stirring in the flask. Monitor the progress of the reaction using TLC
measurements as necessary until the product has formed and the starting materials have been
consumed. You can advance the laboratory time using the clock on the wall. With the electronic lab
book open (click on the lab book on the stockroom counter), you can also save your TLC plates by
clicking Save on the TLC window.
4. When the reaction is complete, “work up” your reaction by first dragging and dropping the separatory
funnel on the flask and then adding H2O to the funnel. Extract the organic layer in the funnel by
clicking on the top layer and dragging it to the cork ring on the lab bench. Your target compound
should now be in this flask.
List the starting materials, solvent, reagent, and products formed:
How long did it take to finish the reaction?
What are the TLC values (Rf) for (a) Starting Materials:
(b) Products:
Write a mechanism for this reaction:
© Beyond Labz, all rights reserved
FTIR and NMR Spectra
After completing a reaction and working up the products, it is still necessary to confirm that the correct
product was formed. The most common tools used for this analysis are Fourier Transform Infrared (FTIR)
and Nuclear Magnetic Resonance (NMR) spectroscopy. In the virtual laboratory, 1H and 13C NMR
spectra are available. Details on interpreting FTIR and NMR spectra are found in your textbook. Your
instructor may or may not ask you to perform this section depending on how your class is structured.
5. To collect an FTIR spectrum of your product, click on the FTIR spectrometer located to the right of
the lab bench and drag the salt plate icon to the flask on the lab bench. A window containing the FTIR
spectrum for your product should now open. Identify the relevant peaks in the FTIR spectrum and
record the position and associated functional group for each in the FTIR table below. The FTIR
spectrum can also be saved to the lab book for later analysis.
FTIR
List position (cm-1) & functional group
4.
1.
5.
2.
6.
3.
7.
6. To collect a 1H NMR spectrum of your product, click on the NMR magnet located to the right of the
chalkboard and drag the NMR sample tube to the flask on the lab bench. A window containing the
NMR spectrum for your product should now open. You can zoom into various portions of the NMR
spectrum by clicking and dragging over the desired area. The Zoom Out button is used to zoom back
out to view the full spectrum. Identify all of the peaks in the NMR spectrum and record the chemical
shift, the splitting, and the number of hydrogens for each peak in the NMR table below. The NMR
spectrum can also be saved to the lab book for later analysis. If necessary to confirm the structure of
your product, you can measure the 13C NMR for the product and record the chemical shifts for the
peaks. Mass spectrometry is also available if needed.
1
H NMR
Peak
Structure:
O
OH
Benzoic acid
†
‡
Chemical
Shift (δ)
Multiplicity†
H‡
Peak
1
7
2
8
3
9
4
10
5
11
6
12
Chemical
Shift (δ)
Multiplicity†
H‡
Specify the multiplicity as a singlet (s), doublet (d), triplet (t), quartet (q), or multiplet (m).
Specify the number of hydrogens associated with each peak.
7. Do the FTIR and NMR spectra you measured and recorded in the tables above confirm that you
synthesized the assigned target compound? Explain.
© Beyond Labz, all rights reserved
8-1: Benzene Nitration – 1
For this assignment, the target compound that you should synthesize is 3-nitro-benzaldehyde. This is an
electrophilic aromatic substitution reaction. Examine the product carefully and determine the substitution
pattern. Which group will already be present in the substrate? Keep in mind the mechanism and how that
will control the selectivity of the process.
Synthesis Procedures
1. Start Virtual ChemLab and select Benzene Nitration – 1 from the list of assignments on the
whiteboard. After entering the synthesis laboratory, use the available reagents on the stockroom shelf
and identify the appropriate starting materials required to synthesize the target compound and add
them to the round bottom flask. Select the appropriate solvent and drag the flask to the Stir Plate on
the lab bench.
2. The round bottom flask containing the starting materials should now be on the stir plate, and the
contents of the flask should be visible on the chalkboard. From the group of reagents found on the lab
bench, select the correct reagent to synthesize the target compound and add it to the flask on the stir
plate. Now attach the heater, condenser, and N2 gas to the round bottom flask so the reaction mixture
can be heated.
3. Start the reaction by clicking on the Stir button on the front of the stir plate. You should be able to
observe the reaction mixture stirring in the flask. Monitor the progress of the reaction using TLC
measurements as necessary until the product has formed and the starting materials have been
consumed. You can advance the laboratory time using the clock on the wall. With the electronic lab
book open (click on the lab book on the stockroom counter), you can also save your TLC plates by
clicking Save on the TLC window.
4. When the reaction is complete, “work up” your reaction by first dragging and dropping the separatory
funnel on the flask and then adding H2O to the funnel. Extract the organic layer in the funnel by
clicking on the top layer and dragging it to the cork ring on the lab bench. Your target compound
should now be in this flask.
List the starting materials, solvent, reagent, and products formed:
How long did it take to finish the reaction?
What are the TLC values (Rf) for (a) Starting Materials:
(b) Products:
Write a mechanism for this reaction:
© Beyond Labz, all rights reserved
FTIR and NMR Spectra
After completing a reaction and working up the products, it is still necessary to confirm that the correct
product was formed. The most common tools used for this analysis are Fourier Transform Infrared (FTIR)
and Nuclear Magnetic Resonance (NMR) spectroscopy. In the virtual laboratory, 1H and 13C NMR
spectra are available. Details on interpreting FTIR and NMR spectra are found in your textbook. Your
instructor may or may not ask you to perform this section depending on how your class is structured.
5. To collect an FTIR spectrum of your product, click on the FTIR spectrometer located to the right of
the lab bench and drag the salt plate icon to the flask on the lab bench. A window containing the FTIR
spectrum for your product should now open. Identify the relevant peaks in the FTIR spectrum and
record the position and associated functional group for each in the FTIR table below. The FTIR
spectrum can also be saved to the lab book for later analysis.
FTIR
List position (cm-1) & functional group
4.
1.
5.
2.
6.
3.
7.
6. To collect a 1H NMR spectrum of your product, click on the NMR magnet located to the right of the
chalkboard and drag the NMR sample tube to the flask on the lab bench. A window containing the
NMR spectrum for your product should now open. You can zoom into various portions of the NMR
spectrum by clicking and dragging over the desired area. The Zoom Out button is used to zoom back
out to view the full spectrum. Identify all of the peaks in the NMR spectrum and record the chemical
shift, the splitting, and the number of hydrogens for each peak in the NMR table below. The NMR
spectrum can also be saved to the lab book for later analysis. If necessary to confirm the structure of
your product, you can measure the 13C NMR for the product and record the chemical shifts for the
peaks. Mass spectrometry is also available if needed.
1
H NMR
Peak
Structure:
O
O 2N
H
3-Nitrobenzaldehyde
†
‡
Chemical
Shift (δ)
Multiplicity†
H‡
Peak
1
7
2
8
3
9
4
10
5
11
6
12
Chemical
Shift (δ)
Multiplicity†
H‡
Specify the multiplicity as a singlet (s), doublet (d), triplet (t), quartet (q), or multiplet (m).
Specify the number of hydrogens associated with each peak.
7. Do the FTIR and NMR spectra you measured and recorded in the tables above confirm that you
synthesized the assigned target compound? Explain.
© Beyond Labz, all rights reserved
6-5: Interpreting NMR Spectra – 4
Interpreting NMR spectra is a skill that often requires some amount of practice, which, in turn,
necessitates access to a collection of NMR spectra. Virtual ChemLab has a spectra library containing
more than 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:
O
_____________________________________________________________
O
_____________________________________________________________
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.
1
H NMR
Structure:
O
1
H NMR
Structure:
O
†
‡
Peak
Chemical
Shift (δ)
Multiplicity†
H‡
Peak
1
7
2
8
3
9
4
10
5
11
6
12
Peak
Chemical
Shift (δ)
Multiplicity†
H‡
Peak
1
7
2
8
3
9
4
10
5
11
6
12
Chemical
Shift (δ)
Multiplicity†
H‡
Chemical
Shift (δ)
Multiplicity†
H‡
Specify the multiplicity as a singlet (s), doublet (d), triplet (t), quartet (q), or multiplet (m).
Specify the number of hydrogens associated with each peak.
© Beyond Labz, all rights reserved
3. To check your predictions, start Virtual ChemLab and select Interpreting NMR Spectra – 4 from the
list of assignments on the whiteboard or click on the Qualitative Analysis bench and click on the
Spectra button on the chalkboard. You should see a list of all the compounds in the spectra library in
alphabetical order by IUPAC name. Mousing over a name in the list will show the structure on the
chalkboard. The four buttons on the side of the list are used to select the different spectroscopic
techniques for the selected compound. Click on the NMR button to display the NMR spectra.
4. Using the Up or Down arrows on the Scroll Bar or dragging the Scroll Bar, 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.
1
H NMR
Structure:
O
1
H NMR
Structure:
O
Peak
Chemical
Shift (δ)
Multiplicity†
H‡
Peak
1
7
2
8
3
9
4
10
5
11
6
12
Peak
Chemical
Shift (δ)
Multiplicity†
H‡
Peak
1
7
2
8
3
9
4
10
5
11
6
12
Chemical
Shift (δ)
Multiplicity†
H‡
Chemical
Shift (δ)
Multiplicity†
H‡
5. 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.
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OV
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Content X Bb VCL Organ x Bb 4902115 X Bb 4902115 X Bb 4902113 X Bb 4902111
C
https://mcphs.blackboard.com/ultra/courses/_38824_1/cl/outline
Introduction
• Give a brief overview of your tasks and purpose in the experiment.
• No more than a paragraph
Type here to search
Bb 4902111
.
X Bb 4902111 X
• Show an understanding of the methods used to acquire data.
Explain what the data means – include relevant numerical values (like the key data points acquired).
• Draw conclusions based on experiment.
• State your accomplishments in the lab.
• If you desire, make a brief editorial comment about the lab.
8:
a
Procedure
•
Write and account of what YOU did in the lab (not what the manual says to do)
• Anyone with your description and a similar understanding of the subject with a rough idea of how the lab should work, should be able to
reproduce YOUR results.
Data and Results
• Report the values you sought in the experiment
• Report values you acquired along the way needed to get your final result.
• Report critical equations used (ie. how to calculate yield, but not how to find the mass of an object by difference)
• Include a short description of how you used certain data to arrive at other pieces of information.
• Any groundbreaking calculations you performed (most calculations belong in an appendix, or can be skipped in the report entirely)
• Graphs and tables, compact, concise, and clear are the ideal way to deliver most of this information.
Discussion
O
Grades – N X +
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• Address any and all questions presented in the lab manual.
• Compare your values with literature values (if available).
• Discuss sources of error and how they might have influenced your results (human error’ and ‘made us be wrong’ don’t qualify).
Conclusion
81°F
[+]
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(4) ENG
4:10 PM
5/19/2022
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