Lab 7: DMAP vs DMAMP
Write me a lab report with the Results & Discussion Section
Lab 7: DMAP vs DMAMP
Write me a lab report with the Results & Discussion Section and an Experimental Paragraph. All the information needed is attached and described below.
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Handout
Attached Files:
Lab 7- Reactivity of 4-(Dimethylamino)pyridine and 4-(Dimethylaminomethyl)pyridine – WebMO version.pdf
This is a 2 week lab.
The first week is just a worksheet thinking about possible outcomes of a reaction.
We will then run that reaction during the second week.
No Pre-lab needed for week 1, just week 2
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Marvinsketch
This is a drawing software used for making organic molecules to include in any assignments there is a fully-online version that lets you draw molecules within a browser window:
https://marvinjs-demo.chemaxon.com/latest/demo.html
Use this to draw any structures you want included in your eventual report
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Tips for planning DMAP/DMAMP report
As you begin to prepare your DMAP/DMAMP lab report, we wanted to share some tips to help with the process.
The second doc attached is a document we sent previous students for tips when writing their report: Pre-DMAP RD comments.pdf
This will give you some tips of formatting you NMR data, and how to properly discuss predictions and outcomes.
Also, below are a series of comment we gave previous students about common mistakes we saw in their reports:
1) Need a name for the product in the experimental paragraph. We uploaded a sheet with all the possible names to Blackboard under the Lab folder. Also, it’s likely that the iodide anion is part of your product so be sure to include that atom in the molecular weight of your product so your percent yield is correctly reported.
2) Need to state what DMAP and DMAMP are (i.e., give the IUPAC name at least once at the beginning of the R&D and the experimental section).
3) Keep the experimental information more general in the discussion. Don’t give detailed information like exact quantities used (unless it is critical to understanding the data) or exact procedures followed. These details should only be in the experimental paragraph.
4) In the experimental paragraph, you dont need to say you did NMR analysis, just list the NMR data.
5) In general, some of the discussions did not accurately convey the prediction process and the various factors you considered. In addition to being too short at times, there were often errors interpreting the data (e.g., mixing up how hybridization and polarizability connect, listing incorrect hybridizations, interpreting the Gaussian data wrong, not discussing both sets of Gaussian results, etc.). Please revisit your data to be sure you are interpreting the data correctly.
6) It would be really helpful to include a graphic of the reactions. It is difficult for the reader to interpret things like N1 and N2 and “top” and “bottom” if they never see a structure. Top and bottom are not good ways of referring to the nitrogens. We have a drawing program, MarvinSketch, to use.
7) Some struggled with clarity and structure to the writing. If the story doesn’t flow well, it will be hard for the reader to follow your data/discussions and therefore it will be hard to understand. It needs to flow and be easily understood. Don’t simply restate the various influences on nucleophilicity as though they exist independently. Actually wrap all effects up into a coherent story. If certain effects give conflicting conclusions, it should be addressed.
8) When interpreting your NMR, be more explicit in not only stating how it is consistent with the structure formed, but what evidence ruled out the other 3 possible products.
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IUPAC names & Pre-comments
Attached Files:
IUPAC Names of DMAP:DMAMP Products.pdf
Pre-DMAP RD comments.pdf
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More Information
In this lab, we were a big group of four. Two of my group members did the experiment for DMAMP. My lab partner and I did this lab with DMAP. Our NMR data is attached below.
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The Procedure That I Wrote Down From The Actual Lab Day
Reaction Setup
1. Place 122mg of 4-(Dimenthylamino) pyridine (nucleophile) into a 25mL round-bottom flask
2. Transfer 2mL of pre-made DCM solution containing CH3I and CH3CH2I into the flask with the nucleophile
3. Swirl the round-bottom flask briefly to mix the contents
Reflux Process
4. Add a boiling chip or place a magnetic stirring bar into the flask
5. Attach a reflux condenser to the round-bottom flask and attach the 2 flexible tubes for the water to go in and out
6. Reflux the solution gently for 30 minutes using a heating mantle set at 30% power
Cooling and Solid Isolation
7. After refluxing, allow the flask to cool to room temp
8. Once cooled, place flask in an ice bath to further cool it down
9. Isolate the solid product by performing vacuum filtration (make sure no water enters the flask during this step)
Rinsing and Drying
10. Rinse the solid with cold CH2Cl2 (2mL each, repeated 3 times for total of 6mL)
11. Continue pulling air through the solid using a vacuum for 3 minutes to dry the product
Weigh and Yield Calculation
12. Weigh isolated solid
13. Calculate percent yield AFTER determining the product structure through analysis (havent done this yet. Pls do this)
Weight of Isolated Solid: 0.483g
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NMR Data
DMAP NMR.pdf
DMAMP NMR (1).pdf
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Writing Guide and Rubric
Attached Files:
Writing Guide – Instructions and Details for Report Submission (1).pdf
Faculty Grading Rubric (Experimental and R&D) (1).pdf