ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 31, Problem 31.15P
Interpretation Introduction
Interpretation: The enantiomer and any two diastereomers of cholesterol are to be drawn, and the position for
Concept introduction: Steroids, a group of tetracyclic lipids composed of one five-membered ring and three six-membered rings. Thesse rings are lettered by A, B, C, and D. Most of the steroids contain two angular methyl groups. These methyl groups are numbered as
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Draw the structure of ,-diethyl--propylthiopentane.
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A. Provide a stepwise mechanism for the formation of nerolidyl pyrophosphate fromfarnesylpyrophosphate B. Provide a stepwise mechanism for the formation of carbocation 1 from nerolidylpyrophosphate. Number the backbone carbons of nerolidyl pyrophosphate from 1 to 11 as shown, andinclude the carbon numbering in your structure of 1 C. Following from B, give an arrow-pushing mechanism to convert 1 to 2 and 2 to 3. Use thebackbone carbon numbering from 1 to indicate where carbon atoms ended up in 2 and 3 D. In addition to forming epi-cedrol, carbocation 3 gives three minor byproducts: a diastereomericalcohol and two alkenes. Draw mechanisms that could give rise to these three products
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Chapter 31 Solutions
ORGANIC CHEMISTRY
Ch. 31 - Problem 31.1
One component of jojoba oil is a wax...Ch. 31 - Problem 31.2
How would you expect the melting...Ch. 31 - Problem 31.3
Draw the products formed when...Ch. 31 - Problem 31.4
The main fatty acid component of the...Ch. 31 - Prob. 31.5PCh. 31 - Problem 31.6
Draw the structure of a lecithin...Ch. 31 - Prob. 31.7PCh. 31 - Problem 31.8
Why are phospholipids, but not...Ch. 31 - Problem 31.9
Explain why regularly ingesting a...Ch. 31 - Problem 31.10
Locate the isoprene units in each...
Ch. 31 - Problem 31.11
Locate the isoprene units in...Ch. 31 - Problem 31.12
Write a stepwise mechanism for the...Ch. 31 - Prob. 31.13PCh. 31 - Prob. 31.14PCh. 31 - Prob. 31.15PCh. 31 - Prob. 31.16PCh. 31 - 31.17 Locate the isoprene units in each...Ch. 31 - Prob. 31.18PCh. 31 - Prob. 31.19PCh. 31 - Prob. 31.20PCh. 31 - Prob. 31.21PCh. 31 - 31.22 What is the structure of an optically...Ch. 31 - Prob. 31.23PCh. 31 - 31.24 Draw the structure of the following...Ch. 31 - Prob. 31.25PCh. 31 - Locate the isoprene units in each compound. a. e....Ch. 31 - 31.27 Classify each terpene and terpenoid in...Ch. 31 - 31.38 Draw the products formed when cholesterol is...Ch. 31 - 31.29 An isoprene unit can be thought of as having...Ch. 31 - 31.30 Draw a stepwise mechanism for the conversion...Ch. 31 - Prob. 31.31PCh. 31 - Prob. 31.32PCh. 31 - Draw three-dimensional structures f or each...Ch. 31 - Prob. 31.34PCh. 31 - Prob. 31.35PCh. 31 - Prob. 31.36PCh. 31 - Prob. 31.37PCh. 31 - 31.38 Draw the products formed when cholesterol is...Ch. 31 - 31.39 Draw a stepwise mechanism for the following...Ch. 31 - 31.40 Draw a stepwise mechanism for the following...Ch. 31 - Prob. 31.41P
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