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
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...
icon
Related questions
Question
100%

Attached. 

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?
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 1 images

Blurred answer
Knowledge Booster
Types of Polymers on the Basis of Physical Properties
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY