Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
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Chapter 6, Problem 35P
Interpretation Introduction
Interpretation: All stereocenters in each structural isomer in previous problems should be identified and the total number of stereoisomers that can exist for the structure should be given.
Concept Introduction: Structural isomers are molecules which have the same molecular formula but have different connectivity of atoms.
Stereocenter is a point in a molecule which bears different substituents. Stereoisomers are two or more compounds which have the same molecular formula and same connectivity of atom butdiffers only in spatial arrangement of their atoms.
The formula for finding maximum number of stereoisomers possible is
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It is easy to imagine a cyclohexane as a flat hexagon and a lot of the time we draw it
that way. Looking at 1,3,5-triethylcyclohexane we cannot tell the stability of the
molecule from looking at the flat 2D drawing. Explain why we need to look at the 3D
configuration and what conformation (axial,equatorial) would each of the three ethyl
groups be in for the most stable configuration.
Stereoisomers share the same connectivity and differ only in the
way their atoms are arranged in space. Draw the structure of a
compound that is a stereoisomer of cis-1,2-
dibromocyclobutane.
(Note that the question asks for a different stereoisomer of the
named compound and not the named compound itself.)
• Use the wedge/hash bond tools to indicate
stereochemistry where it exists.
• In cases where there is more than one answer, just
draw one.
c) For each of the compounds i) to iii) below, identify and draw as many structural
isomers as you can, explaining the type of structural isomerism in each case. For
each structural isomer you draw, explain whether it exhibits stereoisomerism,
stating the type of stereoisomerism where applicable and drawing diagrams of the
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i)
Br₂C=CH₂
CH3CH2CH2CHO
iii)
CH3(CH2) 3CH2Cl
Chapter 6 Solutions
Organic Chemistry: Structure and Function
Ch. 6.2 - Prob. 6.1ECh. 6.2 - Prob. 6.3TIYCh. 6.3 - Prob. 6.4ECh. 6.3 - Prob. 6.5ECh. 6.3 - Prob. 6.6ECh. 6.3 - Prob. 6.7ECh. 6.3 - Prob. 6.8ECh. 6.4 - Prob. 6.10TIYCh. 6.4 - Prob. 6.11ECh. 6.5 - Prob. 6.12E
Ch. 6.5 - Prob. 6.13ECh. 6.6 - Prob. 6.14ECh. 6.6 - Prob. 6.16TIYCh. 6.6 - Prob. 6.17ECh. 6.7 - Prob. 6.18ECh. 6.7 - Prob. 6.19ECh. 6.7 - Prob. 6.20ECh. 6.8 - Prob. 6.21ECh. 6.8 - Prob. 6.22ECh. 6.8 - Prob. 6.23ECh. 6.8 - Prob. 6.24ECh. 6.9 - Prob. 6.26TIYCh. 6.10 - Prob. 6.27ECh. 6.10 - Prob. 6.28ECh. 6 - Prob. 31PCh. 6 - Prob. 32PCh. 6 - Prob. 33PCh. 6 - Prob. 34PCh. 6 - Prob. 35PCh. 6 - Prob. 36PCh. 6 - Prob. 37PCh. 6 - Prob. 38PCh. 6 - Prob. 39PCh. 6 - Prob. 40PCh. 6 - Prob. 41PCh. 6 - Prob. 42PCh. 6 - Prob. 43PCh. 6 - Prob. 44PCh. 6 - Prob. 45PCh. 6 - Prob. 46PCh. 6 - Prob. 47PCh. 6 - Prob. 48PCh. 6 - Prob. 49PCh. 6 - Prob. 50PCh. 6 - Prob. 51PCh. 6 - Prob. 52PCh. 6 - Prob. 53PCh. 6 - Prob. 54PCh. 6 - Prob. 55PCh. 6 - Prob. 56PCh. 6 - Prob. 57PCh. 6 - Prob. 58PCh. 6 - Prob. 59PCh. 6 - Prob. 60PCh. 6 - Prob. 61PCh. 6 - Prob. 62PCh. 6 - Prob. 63PCh. 6 - Prob. 64PCh. 6 - Prob. 65PCh. 6 - Prob. 66PCh. 6 - Prob. 67PCh. 6 - Prob. 68P
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