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Question 2. Zingerone, a naturally occurring compound in fresh ginger, can be synthesized in the laboratory by catalytic hydrogenation of "dehydrozingerone" as shown below. However, one potential problem with this reaction (and many catalytic hydrogenations of unsaturated ketones and aldehydes) is the unintended "over" hydrogenation of both the C=C and the C=0 double bonds, leading to an alcohol product. Но Но НО H2, 5% Pd/C CH3 H3CO CH3 H3CO CH3 H3CO ОН over-hydrogenation alcohol product desired product a) Using 'H NMR, explain how you would identify if the alcohol product has been formed. Only describe the differences that you think would be most obvious in the 'H NMR spectrum. b) Using 1³C NMR, explain how you would identify if the alcohol product has been formed. Only describe the difference(s) that you think would be most obvious in the 1³C NMR spectrum.

Question 2. Zingerone, a naturally occurring compound in fresh ginger, can be synthesized in the laboratory by catalytic hydrogenation of "dehydrozingerone" as shown below. However, one potential problem with this reaction (and many catalytic hydrogenations of unsaturated ketones and aldehydes) is the unintended "over" hydrogenation of both the C=C and the C=0 double bonds, leading to an alcohol product. Но Но НО H2, 5% Pd/C CH3 H3CO CH3 H3CO CH3 H3CO ОН over-hydrogenation alcohol product desired product a) Using 'H NMR, explain how you would identify if the alcohol product has been formed. Only describe the differences that you think would be most obvious in the 'H NMR spectrum. b) Using 1³C NMR, explain how you would identify if the alcohol product has been formed. Only describe the difference(s) that you think would be most obvious in the 1³C NMR spectrum.

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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Question 2. Zingerone, a naturally occurring compound in fresh ginger, can be synthesized in the laboratory by catalytic hydrogenation of "dehydrozingerone" as shown below. However, one potential problem with this reaction (and many catalytic hydrogenations of unsaturated ketones and aldehydes) is the unintended "over" hydrogenation of both the C=C and the C=O double bonds, leading to an alcohol product. НО. Но Но. H2, 5% Pd/C CH3 H3CO CH3 H3CO .CH3 H3COʻ OH over-hydrogenation alcohol product desired product a) Using 'H NMR, explain how you would identify if the alcohol product has been formed. Only describe the differences that you think would be most obvious in the 'H NMR spectrum. b) Using 1°C NMR, explain how you would identify if the alcohol product has been formed. Only describe the difference(s) that you think would be most obvious in the 1³C NMR spectrum.
Transcribed Image Text:Question 2. Zingerone, a naturally occurring compound in fresh ginger, can be synthesized in the laboratory by catalytic hydrogenation of "dehydrozingerone" as shown below. However, one potential problem with this reaction (and many catalytic hydrogenations of unsaturated ketones and aldehydes) is the unintended "over" hydrogenation of both the C=C and the C=O double bonds, leading to an alcohol product. НО. Но Но. H2, 5% Pd/C CH3 H3CO CH3 H3CO .CH3 H3COʻ OH over-hydrogenation alcohol product desired product a) Using 'H NMR, explain how you would identify if the alcohol product has been formed. Only describe the differences that you think would be most obvious in the 'H NMR spectrum. b) Using 1°C NMR, explain how you would identify if the alcohol product has been formed. Only describe the difference(s) that you think would be most obvious in the 1³C NMR spectrum.
c) If you conducted the reaction above and obtained a mixture of the desired and the over- hydrogenation products, what method would you use separate them from each other? Why did you choose this method?
Transcribed Image Text:c) If you conducted the reaction above and obtained a mixture of the desired and the over- hydrogenation products, what method would you use separate them from each other? Why did you choose this method?
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