ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 31, Problem 31.18P
Interpretation Introduction

(a)

Interpretation: The conversion of ball-and-stick model to a skeletal structure that clearly shows the stereochemistry at the ring fusion of given decalin derivative is to be stated.

Concept introduction: Decalin and its derivatives involve fusion of two six-membered rings that share a C−C bond. The substituents present at ring fusion are identified as cis or trans. If substituents present at ring fusion are present opposite sides to each other, then it is identified as trans, and if substituents present at ring fusion are present same sides to each other, then it is identified as cis.

Interpretation Introduction

(b)

Interpretation: The conversion of ball-and-stick model to a skeletal structure that clearly shows the stereochemistry at the ring fusion of given decalin derivative is to be stated.

Concept introduction: Decalin and its derivatives involve fusion of two six-membered rings that share a C−C bond. The substituents present at ring fusion are identified as cis or trans. If substituents present at ring fusion are present opposite sides to each other, then it is identified as trans, and if substituents present at ring fusion are present same sides to each other, then it is identified as cis.

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Draw the products formed when each alkene is treated with BH3 followed by H2O2,HO−. Include the stereochemistry at all stereogenic centers.
Answer the following questions about compounds A–D.a.How are the compounds in each pair related? Choose from constitutional isomers, stereoisomers, or identical molecules: A and B; A and C; B and D. b.Label each compound as a cis or trans isomer. c.Draw B as a hexagon with wedges and dashed wedges to show the stereochemistry of substituents. d.Draw a stereoisomer of A as a hexagon using wedges and dashed wedges to show the orientation of substituents.
Convert each ball-and-stick model to a skeletal structure that clearly shows the stereochemistry at the ring fusion of these decalin derivatives.

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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