Newman as drawn: A HO. conformation: back carbon front carbon rotate back carbon 60 degrees counterclockwise Newman after rotation: C rotate front Newman after rotation: B carbon 180 degrees conformation: conformation: rotate back carbon 120 degrees clockwise Newman after rotation: D Wedge-dash redraw as wedge-dash conformation: Most stable : (least)

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter7: Cycloalkanes
Section: Chapter Questions
Problem 17E: Build a model of methylcyclohexane, and use the model to complete the following Newmanprojections of...
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6. Did you really think I would forget to include Newman projections? Draw the given wedge-
dash structure in a Newman projection (as drawn; do NOT rotate it yet). Then perform the following
rotations, indicating if the resulting conformation is anti staggered, staggered, eclipsed, gauche, or
syn eclipsed. Use abbreviated substituent names for Newman projections and full structures for
wedge-dash projections. Finally, rank the conformers in order of stability (using > or =)
Newman as drawn: A
conformation:
back carbon
front carbon
rotate back carbon 60
degrees counterclockwise
Newman after rotation: C
rotate front
Newman after rotation: B
carbon 180
degrees
conformation:
conformation:
rotate back carbon 120 degrees clockwise
Newman after rotation: D
Wedge-dash
redraw as
wedge-dash
conformation:
Most stable:
(least)
Transcribed Image Text:6. Did you really think I would forget to include Newman projections? Draw the given wedge- dash structure in a Newman projection (as drawn; do NOT rotate it yet). Then perform the following rotations, indicating if the resulting conformation is anti staggered, staggered, eclipsed, gauche, or syn eclipsed. Use abbreviated substituent names for Newman projections and full structures for wedge-dash projections. Finally, rank the conformers in order of stability (using > or =) Newman as drawn: A conformation: back carbon front carbon rotate back carbon 60 degrees counterclockwise Newman after rotation: C rotate front Newman after rotation: B carbon 180 degrees conformation: conformation: rotate back carbon 120 degrees clockwise Newman after rotation: D Wedge-dash redraw as wedge-dash conformation: Most stable: (least)
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