Scribd
Upload
701 views9 pages

Conformations of Alkanes and Cycloalkanes

This document discusses conformations and rotational isomers of alkanes and cycloalkanes. It introduces concepts such as conformations, conformers, and Newman projections that are used to analyze the different temporary molecular shapes that result from bond rotation. Cyclohexane can exist in a more stable chair conformation or less stable boat conformation. For substituted cyclohexanes, equatorial hydrogen atoms are more stable than axial hydrogen atoms in the chair form. An example shows trans-1-tert-butyl-3-methylcyclohexane is more stable when the larger group is equatorial rather than axial.

Uploaded by

Fakhrul Razi
Copyright
© Attribution Non-Commercial (BY-NC)
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PPTX, PDF, TXT or read online on Scribd
701 views9 pages

Conformations of Alkanes and Cycloalkanes

This document discusses conformations and rotational isomers of alkanes and cycloalkanes. It introduces concepts such as conformations, conformers, and Newman projections that are used to analyze the different temporary molecular shapes that result from bond rotation. Cyclohexane can exist in a more stable chair conformation or less stable boat conformation. For substituted cyclohexanes, equatorial hydrogen atoms are more stable than axial hydrogen atoms in the chair form. An example shows trans-1-tert-butyl-3-methylcyclohexane is more stable when the larger group is equatorial rather than axial.

Uploaded by

Fakhrul Razi
Copyright
© Attribution Non-Commercial (BY-NC)
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PPTX, PDF, TXT or read online on Scribd

CONFORMATIONS OF ALKANES AND CYCLOALKANES

Sigma Bonds & Bond Rotation

Two groups bonded by a single bond can undergo rotation about that bond with respect to each other
Conformations temporary molecular shapes result from a rotation about a single bond Conformer each possible structure of conformation Conformational analysis analysis of energy changes occur as a molecule undergoes rotations about single bonds

Newman Projections
H Cl Look from this direction H Cl Et front carbon Et Me H Sawhorse formula OH

Me

combine Me Cl

H Et

OH back carbon

OH Newman Projection

8B. How to Do a Conformational Analysis

Look from this direction H H Ha


c

Hb staggered confirmation H of ethane

CH3 CH3 anti

CH3

CH3

CH3 CH3

gauche

eclipsed

Conformations of Cyclohexane: The Chair & the Boat


3D 1 6 2 5 3 4 2 6 1 (boat form) (less stable) 5 4 3

(chair form) (more stable)

H H
5

H
6

H
2

H H
3

H H
6 4 1

H H
2

HH

HH

Substituted Cyclohexanes: Axial & Equatorial Hydrogen Atoms

Equatorial hydrogen atoms in chair form


H H H H H H

Axial hydrogen atoms in chair form


H H H H

Trans-1-tert-Butyl-3methylcyclohexane
H3C CH3 H3C CH3 (less stable because large group is axial)

H 3C H3C

CH3 CH3 (more stable because large group is equatorial)

ring flip

You might also like