Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 20.6, Problem 12P
Interpretation Introduction
Interpretation:
The two ways that isoprene linkages can be linked head-to-tail to form menthol has to be determined.
Concept Introduction:
Terpenes are made by joining five-carbon units, usually in a head to tail-fashion.
Monoterpenes are those terpenes with two isoprene units-have 10 carbons, sesquiterpenes have 15 carbons, diterpenes have 20 carbons, triterpenes have 30 carbons and tetraterpenes have 40 carbons.
Isopentenyl pyrophosphate is the five-carbon compound used for the biosynthesis of terpenes.
Isoprene unit:
Branched end of isoprene – Head
Unbranched end of isoprene - Tail
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For each reaction below, decide if the first stable organic product that forms in solution will create a new CC bond, and check
the appropriate box.
Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below.
Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions
- just focus on the first stable product you expect to form in solution.
?
Will the first
MgBr
product that forms in this reaction
create a new CC bond?
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Ⓒ No
MgCl
?
Will the first product that forms in this reaction
create a new CC bond?
Click and drag to start drawing a
structure.
Yes
No
X
☐ :
☐
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PH
Assign all the protons
PROPOSE REACTION MECHANISM FOR ACID-CATALYZED REACTION OF 3-PENTANONE WITH DIMETHYLAMINE
Chapter 20 Solutions
Essential Organic Chemistry, Global Edition
Ch. 20.1 - Prob. 1PCh. 20.2 - Prob. 2PCh. 20.2 - Prob. 3PCh. 20.2 - Draw the structure of an optically active fat...Ch. 20.4 - Prob. 6PCh. 20.4 - Prob. 7PCh. 20.4 - The membrane phospholipids in deer have a higher...Ch. 20.4 - Prob. 9PCh. 20.6 - Prob. 10PCh. 20.6 - Prob. 11P
Ch. 20.6 - Prob. 12PCh. 20.7 - Propose a mechanism for the biosynthesis of...Ch. 20.7 - Prob. 14PCh. 20.8 - Draw the individual 1,2-hydride and 1,2-methyl...Ch. 20.9 - Prob. 16PCh. 20 - Prob. 17PCh. 20 - Prob. 18PCh. 20 - Cardiolipins are found in heart muscles. Draw the...Ch. 20 - Prob. 20PCh. 20 - 5-Androstene-3,17-dione is isomerized to...Ch. 20 - Prob. 22PCh. 20 - Prob. 23PCh. 20 - Prob. 24PCh. 20 - Eudesmol is a sesquiterpene found in eucalyptus....
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