1HNMR spectrum from the literature tablelabeled diagram chemical shift (literature), multiplet structure, integration, assignment please all in table based on the data in the labFOR EXAMPLENOChemical shift experimental multipletIntegrationAssignment 17.45 ppm Triplet1Para to Cl27.55 ppmTriplet1Meta to Cl37.56 ppmDoublet1Ortho to Cl47.81 ppmDoublet1Ortho to Cl513.43 ppm Singlet1-COOH Day 2: Recrystallization and Analysis of the o-chlorobenzoic AcidRecrystallize the product using hot toluene. Be sure to add enough toluene so that the solid dissolves at a higher temperature, but some of the solid stays undissolved at room temperature. Do not add too much toluene, as you may not be able to crystallize your product. If you believe you added too much toluene, or if o-chlorobenzoic acid crystals do not appear upon cooling the solution on ice, you will need to evaporate some of the toluene in the hood. The crystals should be suspended fully in toluene before filtration.After drying the solids, determine the melting point of the product. Acquire the infrared spectrum and the ¹H-NMR spectrum in DMSO-d₆.Cleanup Notes: Solid MnO₂ often sticks to the glassware and is difficult to remove, even with soapy water and scrubbing. You can easily clean your glassware, however, by using 12 M HCl. In order not to waste the concentrated acid, transfer your concentrated HCl washings into a large beaker which can be used many times by other students. Clean your ground-glass joints by dipping them into the acid wash solution. To clean your flask, pour the concentrated acid into your flask and swirl. The MnO₂ should be easily removed using these procedures. The acid wash solution can be reused several times by pouring it back into the collection beaker so that it is available to other students.Cleanup Caution: Before you use the concentrated HCl, be sure your flask is rinsed and free of any solid material. Do not leave excess water in the flask. Once your flask is clean and free of loose residue, you can then remove the bound MnO₂, which stains your flask by adding the concentrated HCl. **Day 1: Preparation of o-chlorobenzoic acid**1. **Dissolution and Reaction Setup:** - Dissolve 3.0 g of KMnO₄ in 35 mL of water in a 250-mL round-bottomed flask (caution: KMnO₄ is a skin irritant). - Add about 1.0 g of o-chlorotoluene (approximately 1.00 mL, determined by density). - Attach a water-jacketed condenser, add boiling stones, and reflux the mixture for approximately 1.5 hours.2. **Post-Reaction Filtration:** - After refluxing, collect the filtrate using vacuum filtration with a Büchner funnel. - **Important:** Do not wash with hot or cold water.3. **Handling Insoluble MnO₂:** - MnO₂ byproduct needs to be removed by vacuum filtration. - If the filtrate is purple, the MnO₄⁻ ion is still present. - Add solid sodium bisulfite (NaHSO₃) slowly to reduce the MnO₄⁻. - Continue adding sodium bisulfite until no purple color remains. 4. **Sodium Bisulfite Addition:** - The filtrate may still contain a brownish-black suspension after MnO₄⁻ reduction. - Collect the filtrate again using vacuum filtration to ensure it is colorless (slight brownish hue is acceptable).5. **Acidification:** - Place the colorless filtrate in an ice bath. - Acidify by adding approximately 2.5 mL of concentrated HCl drop by drop while swirling. - Use Litmus paper to ensure the solution is acidic (pH<3).6. **Collection and Storage:** - Precipitated organic product is then collected using vacuum filtration and a Büchner funnel. - Wash the solid material with water to remove any residual solids. - Dry the solid product in an oven until the next lab period for recrystallization.**Important Note:**- If solid material is not obtained during the first lab period, the liquid can be stored until the next session.**Safety Tip:**- The reaction between sodium bisulfite and potassium permanganate is exothermic. Handle with care to avoid heat-related incidents.

1H-NMR is used to determine the structure of the unknown compound. Form the 1H-NMR we can identified…

Answered: 1HNMR spectrum from the literature…

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

NO	Chemical shift experimental	multiplet	Integration	Assignment
1	7.45 ppm	Triplet	1	Para to Cl
2	7.55 ppm	Triplet	1	Meta to Cl
3	7.56 ppm	Doublet	1	Ortho to Cl
4	7.81 ppm	Doublet	1	Ortho to Cl
5	13.43 ppm	Singlet	1	-COOH