Product Obtained see question at the end. Thank you
Data And Report Submission - Pinacol Rearrangement
(4pts) Pinacol Rearrangement
How will you collect data for this experiment?
virtually
Macroscale Pinacol Rearrangement
Dissolve Reactant
From the procedure
Mass of pinacol used (g):
Note: The balance was tared with the weigh
paper before adding pinacol
- Please Help With The 1h Nmr Spectrum For Product Obtained See Question At The End Thank You Data And Report Submission 1 (70.39 KiB) Viewed 39 times
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signals in ppm.
Report Table PR.3: Proton NMR Analysis
2. Use three key signals to justify what compound(s)
that you think are present.
3. Does this suggest that your reaction worked? Use
three key signals to justify your answer.
4. What does this NMR data indicate about the
purity of the product? Use three key signals to justify your
answer.
5. Use the results of your periodic acid and
2,4-DNP tests to justify whether the reaction was a success or a
failure.
6. Draw the mechanism for this reaction and upload
it here.
0.746 0.746 , +O/T- From the procedure 2. To create a hot water bath, add approximately 75 mL of water into a 100 ml beaker and place it on a hot plate to heat to 45-50 °C. 3. Warm the test tube containing the pinacol reaction mixture in the hot water bath to aid in dissolution. Qualitative Tests of Reactant From the procedure Periodic Acid Test 1. Place 2.0 mL of the periodic acid reagent in a clean test tube and add 1 drop of concentrated nitric acid. Mix well. 2. Add 2 drops of the pinacol reaction mixture to the periodic acid mixture and mix well for 5-10 seconds. 3. Add 2 drops of 0.1 M silver nitrate to the periodic acid mixture. Record whether a precipitate forms on the data sheet. 4. Dispose of the contents of the tube for the periodic testi the appropriate waste container and rinse the tube with acetone, disposing of the acetone in the appropriate waste as well. Inspect the following images, making conclusions about the reactant and product mixtures. Note: The presence of a solid is indicated by dots, the color of the solid is indicated by the background of the dotted area. Virtual Periodic Acid Test Key
Virtual Periodic Acid Test Key Negative Test Positive Test Appearance Select the option that best matches your observation for the periodic acid test on the reactant. Periodic Acid Test: Reaction Mixture precipitate From the procedure 2,4-DNP Test 5. Add 2 drops of 2,4-DNP reagent into another clean test tube. 6. Add 5 drops of the pinacol reaction mixture to the 2,4-DNP and mix well. Record whether a precipitate formed on the data sheet. 7. Dispose of the contents of the tube for the 2,4-DNP test in the appropriate waste container and rinse the tube with acetone. Dispose of the acetone in the waste as well.
Virtual 2,4-DNP Test Key Negative Test Positive Test Appearance Select the option that best matches your observation for the 2,4-DNP test on the reactant. 2,4-DNP Test: Reaction Mixture no precipitate Reaction and Work-Up Data Entry From the procedure 1. Slowly add 5.0 mL of sulfuric acid to the pinacol reaction mixture, swirling to mix as you add the acid. This is now your rearrangement product and can be labeled as such. 2. Repeat all the steps of the Qualitative Tests with the reaction product, recording the information on the data sheet. Qualitative Tests of Product Mixture Select the option that best matches your observation for the qualitative tests on the product mixture.
Qualitative Tests of Product Mixture Select the option that best matches your observation for the qualitative tests on the product mixture Periodic Acid Test: Product Mixture no precipitate 2,4-DNP Test: Product Mixture precipitate From the procedure 3. Add 5 mL of tert-butyl methyl ether to the product mixture and mix well. 4. Using a Pasteur pipette, transfer the bottom layer to a clean, dry test tube. 5. Repeat this extraction two more times. Each time use approximately 5 mL of tert-butyl methyl ether. Combine the organic layers resulting in approximately 15 mL of ether solution. 6. Dry the organic layers with anhydrous sodium sulfate. Remember to only add about 0.050 g of the drying agent. Swirl gently. If the drying agent is completely clumped up, add a little more. 7. Measure and record the mass of a clean, dry vial or test tube. 8. Transfer the solution to the tared test tube, leaving the sodium sulfate in the previous tube. 9. Use a light stream of air or a warm water bath to remove the solvent. Perform this in a fume hood. 10. Measure and record the mass of your product. Mass of product obtained (g): Note: The balance was tared with the vial and cap before adding the product
0.575 0.575 g O +O/T+
Mass of reactant used: 0.746 g (1pts) Amount of reactant used in moles 0.0063 mol Saved Mass of product obtained: 0.575 g (1pts) Amount of product obtained in moles 0.0057 mol Saved (2pts) Product theoretical yield (9) 0.631 g Saved (2pts) Product percent yield 91.13% Saved (4pts) Qualitative Tests
Report Table PR.1: Results of Qualitative Tests Table view List view Observation and results for qualitative tests Periodic acid test observation Is a 1,2-diol present? 2,4-DNP test - observation Is a ketone or aldehyde present? Choose... Yes Choose. No Reaction Mixture precipitate no precipitate Choose... No Choose... Yes Product Mixture no precipitate precipitate (10pts) IR Analysis From the procedure 11. Obtain an IR spectrum of the product. IR Spectrum for Product Obtained 1.1 1.0 0.9 0.8 0.7 umm 0.6 Transmitance 0.5 0.4 0.3 0.2 0.1 3500 3000 2500 1500 1000 500 2000 Wavenumbers (cm-1)
Complete the table with 3 Major IR peaks. Saved Normal BIU X2 X EEE fxl 出三 | 留言 | Tx Report Table PR.2: IR Analysis IR Peak, cm1 Bond Type 1700 C=0 streching 2950 sp3 C-H streching 1375 -CH3 bending vibration (2pts) Use 1-2 key peaks to justify what compound(s) that you think are present. Saved Normal BII U X2 X X fx a a BIT IT Tx The IR shows a peak at 2950cm-1 indicating the presence of a sp3 C-H stretching absorption group, additional to that the absence of a peak greater than 3000cm-indicates that there is no sp2 C-H bond. The peak 1700cm-1 indicates the presence of the C=0 stretching absorption group since that occurs 1680-1750. (2pts) Does this suggest that your reaction worked? Use 1 or two key IR peaks to justify your answer. Saved Normal BI IU XzX IE file 田 T 留言 / 7x Yes, the reaction worked since you can clearly see in the reactant has no presence of C=O bond present but here in the product obtained it has C=0 bond presence, sharp peak at 1720 cm-1thus indicating the presence of -C=0 group. You can also see the C-C bond in the obtained product that is not in the reactant which suggests that the reaction is processed. + (2pts) What does this IR data indicate about the purity of the product? Use 1 or two key IR peaks to justify your answer. Saved
(10pts) 'H NMR Analysis From the procedure 12. Dissolve a small amount (-10 mg) of the product in 700 microliters of CDC3, place the solution in an NMR tube and obtain a proton NMR spectrum. TH NMR Spectrum for Product Obtained 우 19H 운 ЗН 3 2 1 0 어 PPM