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 4.4, Problem 4.10TIY
Interpretation Introduction
Interpretation:The origin of the difference of two hydrocarbons is to be defined where A and B are the hydrocarbons and B is more stable than A by 2.3kcal mol-1.
Concept introduction:The stability of these compounds is identified with their conformation i.e. chair or boat conformation.
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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.
4.(a). Draw the structures of (i) cis-1,4-Dibromocyclohexane and (ii) trans-1,4-
Dibromocyclohexane.
4(b). Draw the most stable conformers of (i) cis-1,4-Dibromocyclohexane and (ii)
trans-1,4-Dibromocyclohexane.
4(c)Which is more stable? (i) cis-1,4-Dibromocyclohexane or (ii) trans-1,4-
Dibromolcyclohexane. Explain the reason for your choice.
Draw all the isomers of C5H₁0. Clearly show stereochemistry if stereoisomers are possible.
Step 1: Start by drawing all the isomers with double bonds.
• Consider constitutional isomers, then stereoisomers.
Step 2: Draw all isomers containing a ring.
• Consider constitutional isomers, then stereoisomers.
Step 2: Next consider isomers containing a ring. The largest ring possible with this molecular formula contains 5 carbons, while
the smallest possible ring contains 3 carbons.
Draw an isomer containing a 5-carbon ring.
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/
C
H
Erase
Consider a 4-carbon ring of C5H₁0. Draw stereoisomers,
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Chapter 4 Solutions
Organic Chemistry: Structure and Function
Ch. 4.1 - Prob. 4.1ECh. 4.1 - Prob. 4.3TIYCh. 4.2 - Prob. 4.4ECh. 4.2 - Prob. 4.6TIYCh. 4.3 - Prob. 4.7ECh. 4.4 - Prob. 4.8ECh. 4.4 - Prob. 4.10TIYCh. 4.4 - Prob. 4.11ECh. 4.4 - Prob. 4.12ECh. 4.4 - Prob. 4.14TIY
Ch. 4.6 - Prob. 4.15ECh. 4.7 - Prob. 4.16ECh. 4.7 - Prob. 4.17ECh. 4.7 - Prob. 4.18ECh. 4 - Prob. 21PCh. 4 - Prob. 22PCh. 4 - Prob. 23PCh. 4 - Prob. 24PCh. 4 - Prob. 25PCh. 4 - Prob. 26PCh. 4 - Prob. 27PCh. 4 - Prob. 28PCh. 4 - Prob. 29PCh. 4 - Prob. 30PCh. 4 - Prob. 31PCh. 4 - Prob. 32PCh. 4 - Prob. 33PCh. 4 - Prob. 34PCh. 4 - Prob. 35PCh. 4 - Prob. 36PCh. 4 - Prob. 37PCh. 4 - Prob. 38PCh. 4 - Prob. 39PCh. 4 - Prob. 40PCh. 4 - Prob. 41PCh. 4 - Prob. 42PCh. 4 - Prob. 43PCh. 4 - Prob. 44PCh. 4 - Prob. 45PCh. 4 - Prob. 46PCh. 4 - Prob. 47PCh. 4 - Prob. 48PCh. 4 - Prob. 49PCh. 4 - Prob. 50PCh. 4 - Prob. 51PCh. 4 - Prob. 52PCh. 4 - Prob. 53PCh. 4 - Prob. 54PCh. 4 - Prob. 55PCh. 4 - Prob. 56PCh. 4 - Prob. 57PCh. 4 - Prob. 58PCh. 4 - Prob. 59PCh. 4 - Prob. 60P
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