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Draw a table including this data based on the diagram linked 1H: chemical shift ,  multiplet structure, integration, assignment  13C: chemical shift

Draw a table including this data based on the diagram linked 1H: chemical shift ,  multiplet structure, integration, assignment  13C: chemical shift

Chemistry
Chemistry
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...
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Draw a table including this data based on the diagram linked

1H: chemical shift ,  multiplet structure, integration, assignment 

13C: chemical shift  

 

**Experiment 3: Williamson Ether Synthesis (Data Sheet)** **Setup:** - 4.5 g of potassium hydroxide were dissolved in 8 mL of water in a 250 mL round-bottomed flask. - 2.55 g of p-cresol were added, and the mixture was swirled. - The pale-yellow mixture was brought to gentle reflux, and 6.70 mL of a 50% aqueous solution (g/mL) of α-chloroacetic acid was added drop-wise using a separatory funnel. **Running the Reaction:** - The mixture was refluxed for 10 minutes. **Product Isolation:** - The hot mixture was transferred to a 100 mL beaker, and 10 mL cold water was added. - Concentrated hydrochloric acid was added dropwise until pH<2. - The yellowish mixture was placed in an ice bath for 20 minutes. - The mixture was filtered using a 5 cm Büchner funnel with a vacuum filtration setup. - The crude product was recrystallized from 30 mL hot water. - After filtration, the solids were placed in a drying oven at 100 °C. **Product Characterization:** - 2.30 g of a pale white solid was obtained. - Melting Point (M.p.): 137-140 °C.
Transcribed Image Text:**Experiment 3: Williamson Ether Synthesis (Data Sheet)** **Setup:** - 4.5 g of potassium hydroxide were dissolved in 8 mL of water in a 250 mL round-bottomed flask. - 2.55 g of p-cresol were added, and the mixture was swirled. - The pale-yellow mixture was brought to gentle reflux, and 6.70 mL of a 50% aqueous solution (g/mL) of α-chloroacetic acid was added drop-wise using a separatory funnel. **Running the Reaction:** - The mixture was refluxed for 10 minutes. **Product Isolation:** - The hot mixture was transferred to a 100 mL beaker, and 10 mL cold water was added. - Concentrated hydrochloric acid was added dropwise until pH<2. - The yellowish mixture was placed in an ice bath for 20 minutes. - The mixture was filtered using a 5 cm Büchner funnel with a vacuum filtration setup. - The crude product was recrystallized from 30 mL hot water. - After filtration, the solids were placed in a drying oven at 100 °C. **Product Characterization:** - 2.30 g of a pale white solid was obtained. - Melting Point (M.p.): 137-140 °C.
**NMR Spectra (300 MHz, DMSO-d₆)** This image displays Nuclear Magnetic Resonance (NMR) spectra using DMSO-d₆ as the solvent at a frequency of 300 MHz. It consists of two parts: 1. **¹H-NMR Lower Spectrum**: The lower part of the graph shows the ¹H-NMR spectrum. The x-axis represents the chemical shift in parts per million (ppm), ranging from 12 to 0 ppm. The y-axis represents signal intensity. Notable peaks are observed at several points, indicating different hydrogen environments in the molecule. 2. **¹³C-NMR Upper Spectrum**: The upper part illustrates the ¹³C-NMR spectrum. The x-axis covers a range from 240 to 0 ppm, displaying carbon environments. Peaks seen here provide insight into the carbon framework of the molecule. The spectra exhibit multiple peaks typical for organic compounds, aiding in the identification and analysis of molecular structures. The offset is noted at 1.2 ppm, which may refer to a chemical shift calibration. The combination of both spectra in one image allows for easy comparison and analysis of the corresponding hydrogen and carbon chemical environments within the studied compound.
Transcribed Image Text:**NMR Spectra (300 MHz, DMSO-d₆)** This image displays Nuclear Magnetic Resonance (NMR) spectra using DMSO-d₆ as the solvent at a frequency of 300 MHz. It consists of two parts: 1. **¹H-NMR Lower Spectrum**: The lower part of the graph shows the ¹H-NMR spectrum. The x-axis represents the chemical shift in parts per million (ppm), ranging from 12 to 0 ppm. The y-axis represents signal intensity. Notable peaks are observed at several points, indicating different hydrogen environments in the molecule. 2. **¹³C-NMR Upper Spectrum**: The upper part illustrates the ¹³C-NMR spectrum. The x-axis covers a range from 240 to 0 ppm, displaying carbon environments. Peaks seen here provide insight into the carbon framework of the molecule. The spectra exhibit multiple peaks typical for organic compounds, aiding in the identification and analysis of molecular structures. The offset is noted at 1.2 ppm, which may refer to a chemical shift calibration. The combination of both spectra in one image allows for easy comparison and analysis of the corresponding hydrogen and carbon chemical environments within the studied compound.
Expert Solution
Step 1

Proton NMR: COOH at delta 12.0, aromatic region at delta 6.5 to 8.0, oxygen attached carbon having hydrogens at delta 3.5 to 4.0.

13CNMR: carbonyl of COOH at delta 170. aromatic region at delta 110 to 160, oxygen attached carbons at delta 60 to 70.

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