Expert answer:Synthesis of 2-methoxynaphthalene via an Sn2 React
Expert answer:the report for this experiment should follow the following guidelines: 1. The entire report should be typed with 1.5 line spacing, including a reaction scheme
and any organic chemical structures. a. Learn how to make subscripts and superscripts with your word processor. b. Learn to use MarvinSketch. The synthesis scheme(s) MUST be your own
work. Do not share a scheme with someone else. You can install the program
on your personal computer by Downloading Marvin Beans at:
https://www.chemaxon.com/download/marvin-suite/. c. The font size should be 12, and the pages should have 1” margins.
2. The title page should show the title of the experiment, your name and lab section, the
dates the experiment was conducted, and the course name and number. 3. The pages should be numbered starting on page 2. The numbers should appear at the
top right or the bottom center of the page. 4. Be sure to use correct grammar, including complete sentences. Use a “neutral voice”:
avoid the first person, except when very awkward. Since you will be discussing an
experiment you have already done, all narrative should be in the past tense. 5. Always use your own words! Do NOT work on this report with your any other
classmate. Likewise, do not copy material out of the laboratory manual. 6. Use appropriate headings to separate the sections of the report. The separate sections
should include the following:
Introduction
Give a brief statement about the experiment. Provide an introduction to your
reaction. Describe the reaction sequence in words (but remember this is not the
place for the procedure), and then provide a complete reaction scheme. Be sure to
use a chemical drawing program NOT molecular formulas. The synthetic scheme
must be your own work. Provide a brief introduction to Sn2 reactions. Discuss
why the final product of your reaction may be commercially useful? Discuss the
importance of Green Chemistry and how that relates to the greening of reaction
conditions.
Procedure
Present the complete procedure YOU used in the synthesis of your product and
the following analysis and applications. Include observations and also discuss
any problems you encountered. This should be in paragraph format NOT an
outline.
Results and Conclusions
Use boxed, clearly-labeled tables with grid-lines to present all of the results of
your synthesis and the data obtained. Be sure to include theoretical yield, percent
yield, appearance of the product, summary of important IR peaks, boiling/melting
points, and TLC results, if any.
Scan and imbed all your IR spectra and TLC plates into the report. The scanned
images should be treated as numbered figures in the text of the document.
Then provide a brief discussion of your results referring to the numbers in your
tables and figures. Be sure to include a discussion of how you know that the
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synthesis was successful. Also, provide suggestions for further greening the
experiment. In this discussion you must address three of these five areas:
alternate alcohol, alternate alkyl halide, alternate reagent, alternate solvent,
alternate reaction conditions. Think about the twelve principles of green
chemistry and the green metrics when you answer this question. This is what we
need to do in order to spread the word about greening chemistry!!!
References
References should follow the format:
Author, Title of publication, Publisher, Date, Page numbers
You should use in-text citations to denote the information you obtained from
specific references. Use a superscript or number in parentheses after the
particular information obtained from the reference, and then number your
references accordingly and in sequence at the end of the report. List all sources,
including the lab text. 7. Some miscellaneous comments: a. Do not capitalize names of chemicals unless they start the sentence. b. Avoid beginning sentences with numbers: find some creative,
grammatically-correct way to begin each sentence some other way. c. Put a space between a numerical value and its unit (2.5 mL not 2.5mL). d. All numbers, whether in scientific notation or not, should have at least one
digit before the decimal: “0.58 g” not “.58 g”. e. When discussing possible errors or problems, do not use the term “human
error” or “experimental error”: be specific! f. Before printing your report, make sure that headings are not cut off at the
bottom of a page. This also applies to tables: in fact, for short tables, try to
have the entire table together on one page. g. Use abbreviations correctly. Some common ones are:
L (liter), mL (milliliter)
g (gram), mg (milligram)
m (meter), mm (millimeter), nm (nanometer)
M (molar)
mol (mole)
K (not °K) for Kelvin °C (even in the narrative, do not write “degrees Celsius”: use the abbreviation)
s (second), min (minute), h (hour)
h. Be careful about significant figures. A three-place weight of an acid will
not yield a five-place calculation of percent yield.
12principlesgreenchem.pdf
exp6_synthesisviasn2.pdf
ir_frequency.pdf
Unformatted Attachment Preview
The Twelve Principles of Green Chemistry
Develped by Paul T. Anastas and John C. Warner
1. It is better to prevent waste than to treat or clean up waste after it is formed.
2. Synthetic methods should be designed to maximize the incorporation of all materials used
in the process into the final product.
3. Wherever practicable, synthetic methodologies should be designed to use and generate
substances that possess little or no toxicity to human health and the environment.
4. Chemical products should be designed to preserve efficacy of function while reducing
toxicity.
5. The use of auxiliary substances (e.g. solvents, separation agents, etc.) should be made
unnecessary wherever possible and innocuous when used.
6. Energy requirements should be recognized for their environmental and economic impacts
and should be minimized. Synthetic methods should be conducted at ambient
temperature and pressure.
7. A raw material or feedstock should be renewable rather than depleting wherever
technically and economically practicable.
8. Unnecessary derivatization (blocking group, protection/deprotection, temporary
modification of physical/chemical processes) should be avoided whenever possible.
9. Catalytic reagents (as selective as possible) are superior to stoichiometric reagents.
10. Chemical products should be designed so that at the end of their function they do not
persist in the environmental and break down into innocuous degradation products.
11. Analytical methodologies need to be further developed to allow for real-time, in-process
monitoring and control prior to the formation of hazardous substances.
12. Substances and the form of a substance used in a chemical process should be chosen so as
to minimize the potential for chemical accidents, including releases, explosions, and fires.
Experiment 6
Synthesis of 2-methoxynaphthalene via an Sn2 Reaction
Required Reading
Zubrick: Chapter 22
Zubrick: Chapter 32
Reflux and Addition
Infrared Spectroscopy
Reaction
In this experiment you will be performing an Sn2 reaction using 2-naphthol as the
nucleophile and methyl iodide as the substrate.
OH
OCH3
1) NaOH, EtOH
reflux
2) CH3I
2-Naphthol
2-methoxynaphthalene
Scheme 1. Sn2 reaction between 2-naphtol and methyl iodide to produce 2-methoxynaphthalene.
Procedure
Reaction (Week 1)
To a 100 mL round bottom flask (RBF), add 0.56 g (14.0 mmol) of ground sodium
hydroxide (about 5 or 6 pellets) and 1.0 g (6.9 mmol) of 2-naphthol. Add 20 mL ethanol
and a stir bar. Swirl the flask. Place a reflux condenser on the flask then reflux and stir
the solution for 15 minutes or until all of the solids have dissolved (Zubrick: Figure 22.1).
After this time, remove the heat source and allow the solution to cool slightly.
CAUTION: Make sure the solution has stopped boiling before proceeding to the
following step. After the solution has stopped boiling, remove the reflux condenser and
add 0.9 mL methyl iodide (8.8 mmol) to the RBF. Replace the condenser and reflux for
an additional hour. Check the reaction for completion by TLC by taking a small amount
from the reaction mixture after 30 and 60 minutes using a Pasteur pipet.
While the solution is refuxing, cool 50 mL of water in an ice bath for later use.
Prepare a TLC chamber by placing a piece of filter paper inside the TLC chamber. Pour
5 mL of 70:30 hexane:ethyl acetate solution into the chamber and replace the TLC
chamber lid. Prepare a TLC plate and label three lanes as N, 30, 60. Prepare a 2%
solution of 2-naphthol in hexane. Spot this solution in the N lane of TLC. Spot the
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reaction mixture after 30 and 60 minutes. Develop the TLC. Visualize the TLC plate
under the UV lamp.
Purification (Week 1)
After 60 minutes of refluxing, remove the heat source and carefully pour the contents of
the RBF over about 25 g of ice in a 250 mL beaker. Using the 50 mL of water that has
been cooling, rinse the RBF and add this to the beaker containing the ice and your
product. Swirl the contents of the beaker until all of the ice has melted. Collect the
product by vacuum filtration. Wash the product with ice-cold water. Draw air through
the product for 5-10 minutes. If additional product crystallizes out of the filtrate, collect
it by vacuum filtration and combine all of the product. Allow your product to dry over
the next week.
Characterization (Week 2)
Weigh and analyze your product by IR, MP, and a 2nd TLC.
Acknowledgements
Modified from J.J. Esteb, J.R. Magers, L. McNulty, P. Morgan, A.M. Wilson, J. Chem.
Ed. 2009, 86, 850–852.
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Functional Group
Alkanes
C–H
C–C
Alkenes
=C–H stretch
=C–H bend
C=C
Alkynes
≡C–H
C≡C
Alkyl halides
C–Cl
C–Br
C–I
Alcohols
O–H
C–O
Amines
N–H
C–N
Aromatics
C–H stretch
C–H bend
C=C
Carbonyls (C=O)
Ketones
Aldehydes
Esters
Amides
Acids
Acid Anhydride
Acid Chlorides
Nitrile (C≡N)
Nitro (NO2)
Frequency (cm-1)
Intensity and Comments
2980-2850
1480-1420
medium to strong
medium
3150-3000
980-960 (trans)
730-665 (cis)
1680-1600
medium; very weak for trans
strong
strong
weak to medium
3350-3300
2260-2100
strong
weak to medium
800-600
600-500
500
strong
strong
strong
3650-3300
1350-1050
strong and broad
strong
3500-3100
~1200
medium and strong; 1° amines-2 bands; 2° amines-1 band
medium
3080-3020
900-730
1650-1580
weak to medium
strong
weak to medium
1730-1700
1730-1700
1750-1735
1680-1630
1730-1700
1850-1740
1820-1770
2200-2250
Doublet at:
1570-1550 &
1380-1360
strong
strong; also has a O=C-H doublet at ~2700 & 2800 cm1
strong; also has C–O stretch
strong; 1° and 2° amides also have N-H stretch
strong; also has O–H stretch
strong; doublet
strong
medium
strong
…
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