EBK ORGANIC CHEMISTRY
9th Edition
ISBN: 8220100591310
Author: McMurry
Publisher: CENGAGE L
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Chapter 27.7, Problem 10P
Interpretation Introduction
Interpretation:
The structures of lanosterol and cholesterol are to be compared and the changes needed for their interconversion are to be listed.
Concept introduction:
Lanosterol and cholesterol differ in the position of the double bonds, in the number of methyl groups and in the nature of the side chain. By looking at their structures the differences between them can be listed.
To compare:
The structures of lanosterol and cholesterol and to list the changes needed for their interconversion.
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Would the following organic synthesis occur in one step? Add any missing products, required catalysts, inorganic reagents, and other important conditions. Please include a detailed explanation and drawings showing how the reaction may occur in one step.
This organic molecule is dissolved in an acidic aqueous solution:
OH
OH
A short time later sensitive infrared spectroscopy reveals the presence of a new C = O stretch absorption. That is, there must now be a new molecule present
with at least one C = O bond.
In the drawing area below, show the detailed mechanism that could convert the molecule above into the new molecule.
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Curved arrows are used to
illustrate the flow of electrons.
Use the reaction conditions
provided and follow the curved
arrows to draw the product of
this carbocation rearrangement.
Include all lone pairs and
charges as appropriate.
H
1,2-alkyl shift
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Chapter 27 Solutions
EBK ORGANIC CHEMISTRY
Ch. 27.1 - Carnauba wax, used in floor and furniture...Ch. 27.1 - Draw structures of glyceryl tripalmitate and...Ch. 27.2 - Prob. 3PCh. 27.2 - Write the saponication reaction of glyceryl...Ch. 27.4 - Prob. 5PCh. 27.5 - Prob. 6PCh. 27.5 - Prob. 7PCh. 27.6 - Draw the following molecules in chair...Ch. 27.6 - Lithocholic acid is an A–B cis steroid found in...Ch. 27.7 - Prob. 10P
Ch. 27.SE - Prob. 11VCCh. 27.SE - Propose a biosynthetic pathway for the...Ch. 27.SE - Identify the following fatty acid, and tell...Ch. 27.SE - Prob. 14MPCh. 27.SE - Prob. 15MPCh. 27.SE - Prob. 16MPCh. 27.SE - Prob. 17APCh. 27.SE - Fats can be either optically active or optically...Ch. 27.SE - Prob. 19APCh. 27.SE - Show the products you would expect to obtain from...Ch. 27.SE - Draw a Newman projection along the C2-C3 bond of...Ch. 27.SE - The plasmalogens are a group of lipids found in...Ch. 27.SE - Prob. 23APCh. 27.SE - Prob. 24APCh. 27.SE - Prob. 25APCh. 27.SE - Prob. 26APCh. 27.SE - Prob. 27APCh. 27.SE - Prob. 28APCh. 27.SE - Prob. 29APCh. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Prob. 34APCh. 27.SE - Draw the most stable chair conformation of...Ch. 27.SE - Draw the most stable chair conformation of...Ch. 27.SE - Prob. 37APCh. 27.SE - Prob. 38APCh. 27.SE - Prob. 39APCh. 27.SE - What product would you obtain by reduction of...Ch. 27.SE - Prob. 41APCh. 27.SE - Eleostearic acid, C18H30O2, is a rare fatty acid...Ch. 27.SE - Prob. 43APCh. 27.SE - Prob. 44APCh. 27.SE - Propose a synthesis of diethylstilbestrol (Problem...Ch. 27.SE - Prob. 46APCh. 27.SE - Cembrene, C20H32, is a diterpenoid hydrocarbon...Ch. 27.SE - α-Fenchone is a pleasant-smelling terpenoid...Ch. 27.SE - Prob. 49APCh. 27.SE - Propose a mechanism for the biosynthesis of the...
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