Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN: 9780618974122
Author: Andrei Straumanis
Publisher: Cengage Learning
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Chapter 6, Problem 22E

Double bonds do not rotate freely under normal conditions. The change from Z to E requires areaction. This can occur in the presence of a catalyst or with the addition of a large amount ofenergy (e.g., at high temperature).
One such reaction is diagramed below:
(1) Add enough potential energy to break the double bond ( E act ) .
(2) free rotation occurs at high energy transition state, then
(3) reforming the double bond as a mixture of Z and E.
Draw E-2-butene in one box and Z-2-butene in the other box, and explain your reasoning.
Chapter 6, Problem 22E, Double bonds do not rotate freely under normal conditions. The change from Z to E requires

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(a) Using Newman projections, draw all staggered and eclipsedconformations that result from rotation around the bond highlighted in red in each molecule; (b) draw a graph of energy versus dihedral angle for rotation around this bond.
5. For the pair of compounds circle the compound which is more stable (you may find it helpful to draw out the chair conformation)
is this (Z) or (E) conformation, and how do you know?

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Organic Chemistry: A Guided Inquiry

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