CHEM2720 Howard College Nucleophilic Substitution Reactions Paper Write a formal lab report. I have attached the rubric to work with. I will provide a samp

CHEM2720 Howard College Nucleophilic Substitution Reactions Paper Write a formal lab report. I have attached the rubric to work with. I will provide a sample paper if needed. please use professional drawing software to show reactions and mechanisms. MarvinSketch has a free option you can download for Mac or Windows. Drawings can be exported as picture files and copied into Microsoft Word or other programs. You just need to create an account on their website first.https://chemaxon.com/products/marvin/download CHEM 2720 Lab #6
Nucleophilic Substitution Reactions: SN1 and SN2
Introduction
Nucleophilic substitution reactions are very common and versatile organic chemistry
reactions. In this lab you will compare several factors that will influence how well each
mechanism works.
Substrate
The substrate may contain a primary (1˚), secondary (2˚), or tertiary (3˚) leaving group.
Because SN1 reactions work by forming a carbocation intermediate, the substrate must
be secondary (2˚) or tertiary (3˚) in order for the intermediate to be stable. As SN2
reactions work by direct backside attack by a nucleophile, steric hinderance must be
considered and only primary (1˚) and secondary (2˚) substrates work well.
Leaving Group
For both SN1 and SN2 reactions, the leaving group need to be stable on its own ofter
leaving the molecule. There may be a noticeable difference between the reaction rate
when the leaving group is Cl versus Br.
Nucleophile
Both reactions are favored by a good nucleophile, but the nucleophile is more
important in the SN2 reaction. In SN2 the nucleophile needs to attack the carbon
directly, where in SN1 the carbocation is a very easy target and a weak nucleophile will
work.
Solvent
Protic solvents are those with the ability to form hydrogen bonds, while aprotic
solvents do not have this ability. Protic solvents are important in SN1 reactions as they
help separate and stabilize the carbocation and leaving group. Protic solvents act to
block the path from nucleophile to substrate in SN2 reactions, so aprotic solvents work
best in those cases.
Pre-Lab Preparation
1. In your lab notebook, prepare a list of all chemicals with which you will be working.
a) List any and all hazards associated with each chemical.
b) List all relevant physical constants for each chemical.
c) List any other precautions for this lab.
2. In your lab notebook, make a detailed list of all waste that will be generated in this
lab and how to dispose of it.
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CHEM 2720 Lab #6
Pre-Lab Questions
1. What is the nucleophile in the reactions using AgNO3 in ethanol?
2. What is the nucleophile in the reactions using NaI in acetone?
3. Draw one (1) mechanism from each part of the experiment. Choose the one you
believe most likely to occur in each part.
Procedure
1. Work in groups of two (2). You will mix the reactants in test tubes and observe the
time it takes for the reactions to complete. Be ready to measure the reaction times
in seconds. Some reactions will finish almost instantly and other will take longer or
may not react at all. Reaction completion is determined by the appearance of a
precipitate in the test tube. If a precipitate does not form within a few minutes of
mixing, set it aside and periodically check on it to see if there are changes. After 30
minutes, if there is still no change, you may say there was no reaction (NR). For
each part, record your observations in table format in your lab notebook.
Part 1 SN2 reaction rate as a function of substrate
2. Add 6mL of 15% NaI in acetone into three (3) test tubes. Add six (6) drops of 1bromobutane to the first, six (6) drops of 2-bromobutane to the second, and six (6)
drops of 2-bromo-2-methylpropane to the third.
3. Gently swirl or shake the tubes and monitor the reactions for the appearance of a
precipitate.
Part 2 SN1 reactions as a function of substrate
4. Add 6mL of 0.1M AgNO3 in ethanol into three (3) test tubes. Add six (6) drops of 1bromobutane to the first, six (6) drops of 2-bromobutane to the second, and six (6)
drops of 2-bromo-2-methylpropane to the third.
5. Gently swirl or shake the tubes and monitor the reactions for the appearance of a
precipitate.
Part 3 Secondary steric effects on SN2 reactions
6. Add 6mL of 15% NaI in acetone into two (2) test tubes. Add twelve (12) drops of 1bromobutane to the first and twelve (12) drops of 1-bromo-2-methylpropane to the
second.
7. Gently swirl or shake the tubes and monitor the reactions for the appearance of a
precipitate.
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CHEM 2720 Lab #6
Part 4 SN2 reactions as a function of leaving group
8. Add 5mL of 15% NaI in acetone to two (2) test tubes. Add 10 drops of 1bromobutane to one tube and 10 drops of 1-chlorobutane to the other.
9. Gently swirl or shake the tubes and monitor the reactions for the appearance of a
precipitate.
Part 5 SN1 reactions as a function of leaving group
10. Add 5mL of 0.1M AgNO3 in ethanol to two (2) test tubes. Add 5 drops of 2bromo-2-methylpropane to one tube and 5 drops of 2-chloro-2-methylpropane to
the other.
11. Gently swirl or shake the tubes and monitor the reactions for the appearance of a
precipitate.
Part 6 SN2 reactions as a function of substrate concentration
12. Add 10mL of 15% NaI in acetone to two (2) test tubes. Add 2mL of 1.0M 1bromobutane to one tube and 2mL of 2.0M 1-bromobutane to the other.
13. Gently swirl or shake the tubes and monitor the reactions for the appearance of a
precipitate.
Part 7 SN2 reactions as a function of nucleophile concentration
14. Add 10mL of 1.0M 1-bromobutane to two (2) test tubes. Add 2mL of 7.5% NaI in
acetone to one and 2mL of 15% NaI in acetone to the other.
15. Gently swirl or shake the tubes and monitor the reactions for the appearance of a
precipitate.
Part 8 SN1 reactions as a function of substrate concentration
16. Add 3mL of 0.01M 2-chloro-2-methylpropane to a test tube and 3mL of 0.1M 2chloro-2-methylpropane to another. Add 6mL of 0.1M AgNO3 in ethanol to both
test tubes.
17. Gently swirl or shake the tubes and monitor the reactions for the appearance of a
precipitate.
Part 9 SN2 reactions as a function of solvent
18. Add 4mL of 1.0M 1-bromobutane to two (2) test tubes. Add 2mL of 15% NaI in
acetone to one and 2mL of 15% NaI in ethanol to the other.
19. Gently swirl or shake the tubes and monitor the reactions for the appearance of a
precipitate.
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CHEM 2720 Lab #6
Post-Lab
1. You will complete a formal lab report for this experiment and therefore there are no
post-lab questions for you to answer in your lab notebook.
6-4
Organic Chemistry Lab Report Instructions and Rubric
The Final Project Report
The report should have the following components:
•
•
•
•
•
•
•
•
Title
Objective (what are you trying to accomplish)
Introduction
o This will include a description of the technique(s) used and the theory of
how they work. Also include what data the instruments are able to
generate and why they are relevant to your sample. Relevant reactions
and mechanisms should go here.
List of materials (this does not need to be in paragraph form)
Procedure
o Reference the lab manual and list any changes made in lab
Results
o This section should include tables, lists, and observations made with each
experiment you performed. Refer back to the procedure when necessary
for clarity.
Conclusion
o This is the most important section, where you will discuss your data and
present your findings. Refer to the results section when discussing specific
aspects of your experiments. Explain your conclusion and how each
experiment and piece of data helped you arrive at the conclusion.
References
o Any explanations and theory presented should give credit to the source
where you found the information. If your source is our text, then cite it. If
your source is lecture slides, cite them. Other sources are welcome.
Grading Rubric
Please refer to the rubric below when writing your report. I will use the same rubric to
grade each of your projects. This will give you an idea of what I expect and what I look
for when grading. Also, you will get an idea of what an “A” project looks like versus a
“C” project.
1
Organic Chemistry Lab Report Instructions and Rubric
Report
structure
Introduction
Results
Conclusion
Excellent: all
described outcomes
are met, are thorough,
and are complete
Good: most
outcomes are met,
are thorough, and
are complete
Fair: some
outcomes are
met, and may
be incomplete
Needs
Improvement:
Outcomes are not
met, are not
complete, and
some items are
missing
All sections described
above are present and
complete. References
are included.
Some sections
might be missing
or be slightly
incomplete.
References are
included.
The structure
does not follow
the description
above. Citations
are not present.
4 points
3 points
Some sections
might be
missing and
incomplete.
Some work
might not be
cited.
2 points
This section clearly
informs the reader
about the theory
behind each technique
to be used and the
value of each
technique to the
experiment
7-8 points
The reader gets a
good sense of
what techniques
will be used and a
general idea of
how they apply to
the experiment
Relevant
background
information is
missing
relating to the
techniques to
be used.
Connection is
missing between
this section and
the experiment.
Little information
is presented on
the techniques
used.
0-2 points
Results are presented
in list and/or table
format. Observations
are clearly written.
Results are
presented. Tables
or lists might be
absent.
Observations are
clearly written.
5-6 points
4 points
3 points
Conclusion references
the original question.
The results section is
referenced often to
logically explain how a
conclusion was
reached.
Conclusion
references the
original question.
The results are
referenced
sometimes.
7-8 points
5-6 points
3-4 points
0-1 point
Some results
are missing.
Tables or lists
are not used.
Observations
might be
missing.
2 points
Section is
disorganized,
data is missing,
observations
might be missing.
Conclusion
might not
clearly relate to
original
question. The
link between
the results and
conclusion is
not clear.
3-4 points
Conclusion is not
logically
supported by the
data. The
original question
was not
addressed.
0-1 point
0-2 points
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