Consider 1-bromopropane,  CH3CH2CH2Br. (a) Draw a Newman projection for the conformation in which ­ CH3 and -Br are anti (dihedral angle 180°). (b) Draw Newman projections for the conformations in which - CH3 and -Br are gauche (dihedral angles 60° and 300°). (c) Which of these is the lowest energy conformation? (d) Which of these conformations, if any, are related by reflection?

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter2: Alkanes And Cycloalkanes
Section2.6: Cis,trans Isomerism In Cycloalkanes And Bicycloalkanes
Problem 2.13P: Following is a planar hexagon representation for one isomer of 1,2,4-trimethylcyclohexane. Draw the...
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Consider 1-bromopropane,  CH3CH2CH2Br.

(a) Draw a Newman projection for the conformation in which ­ CH3 and -Br are anti (dihedral angle 180°).

(b) Draw Newman projections for the conformations in which - CH3 and -Br are gauche (dihedral angles 60° and 300°).

(c) Which of these is the lowest energy conformation?

(d) Which of these conformations, if any, are related by reflection?

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