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A researcher employed at Phenomenal Phenols, Inc. has been asked by her supervisor, O. H. Gruppa, to identify a compound A that was isolated from natural sources. Compound A, mp 129-130 °C, is soluble in NaOH solution and in hot water. The IR spectrum of compound A shows prominent absorptions at 3300-3600 cm- (broad) and 1680 cm1; the EI mass spectrum of compound A has prominent peaks at mlz = 166 and 107, and the CI mass spectrum has an M+1 peak at m/z = 167. The NMR spectrum of compound A is given. Titration determined that compound A has two acidic groups with pK values of 4.7 and 10.4. The UV spectrum of compound A is virtually unchanged as the pH of a solution of compound A is raised from 2 to 7, but the Amax shifts to much higher wavelength when compound A is dissolved in 0.1 M NAOH solution. chemical shift, Hz 2400 2100 1800 1500 1200 900 600 300 2H 1H low-field region: 2H 7.7 Hz 1H 7.7 Hz 2H 13 12 11 10 9 Ppm (8) 2H 4. chemical shift, ppm (8) 8 1

A researcher employed at Phenomenal Phenols, Inc. has been asked by her supervisor, O. H. Gruppa, to identify a compound A that was isolated from natural sources. Compound A, mp 129-130 °C, is soluble in NaOH solution and in hot water. The IR spectrum of compound A shows prominent absorptions at 3300-3600 cm- (broad) and 1680 cm1; the EI mass spectrum of compound A has prominent peaks at mlz = 166 and 107, and the CI mass spectrum has an M+1 peak at m/z = 167. The NMR spectrum of compound A is given. Titration determined that compound A has two acidic groups with pK values of 4.7 and 10.4. The UV spectrum of compound A is virtually unchanged as the pH of a solution of compound A is raised from 2 to 7, but the Amax shifts to much higher wavelength when compound A is dissolved in 0.1 M NAOH solution. chemical shift, Hz 2400 2100 1800 1500 1200 900 600 300 2H 1H low-field region: 2H 7.7 Hz 1H 7.7 Hz 2H 13 12 11 10 9 Ppm (8) 2H 4. chemical shift, ppm (8) 8 1

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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A researcher employed at Phenomenal Phenols, Inc. has been asked by her supervisor, O. H. Gruppa, to identify a compound A that was isolated from natural sources. Compound A, mp 129–130 °C, is soluble in NaOH solution and in hot water. The IR spectrum of compound A shows prominent absorptions at 3300–3600 cm-1 (broad) and 1680 cm1; the EI mass spectrum of compound A has prominent peaks at mlz = 166 and 107, and the CI mass spectrum has an M + 1 peak at m/z = 167. The NMR spectrum of compound A is given. Titration determined that compound A has two acidic groups with pKa values of 4.7 and 10.4. The UV spectrum of compound A is virtually unchanged as the pH of a solution of compound A is raised from 2 to 7, but the Amax shifts to much higher wavelength when compound A is dissolved in 0.1 M NAOH solution. chemical shift, Hz 2400 2100 1800 1500 1200 900 600 300 2H 1H low-field region: 2H 7.7 Hz 1H 7.7 Hz 2H 12 11 10 9 Ppm (8) 13 2H 8 7 6. 4 1 chemical shift, ppm (8) Propose a structure for compound A.
Transcribed Image Text:A researcher employed at Phenomenal Phenols, Inc. has been asked by her supervisor, O. H. Gruppa, to identify a compound A that was isolated from natural sources. Compound A, mp 129–130 °C, is soluble in NaOH solution and in hot water. The IR spectrum of compound A shows prominent absorptions at 3300–3600 cm-1 (broad) and 1680 cm1; the EI mass spectrum of compound A has prominent peaks at mlz = 166 and 107, and the CI mass spectrum has an M + 1 peak at m/z = 167. The NMR spectrum of compound A is given. Titration determined that compound A has two acidic groups with pKa values of 4.7 and 10.4. The UV spectrum of compound A is virtually unchanged as the pH of a solution of compound A is raised from 2 to 7, but the Amax shifts to much higher wavelength when compound A is dissolved in 0.1 M NAOH solution. chemical shift, Hz 2400 2100 1800 1500 1200 900 600 300 2H 1H low-field region: 2H 7.7 Hz 1H 7.7 Hz 2H 12 11 10 9 Ppm (8) 13 2H 8 7 6. 4 1 chemical shift, ppm (8) Propose a structure for compound A.
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