Structure of Cyclohexane (C5H12).

Cyclohexane is the most stable alicyclic ring system. The cyclohexane ring
exist in the non planar conformation to avoid the angle strain.

Chair Form Boat Form

Structure of Cyclohexane (C5H12).

Chair Form Boat Form

Half Chair Form Twisted

• In cyclohexane, three C atoms pucker up and three C
atoms pucker down, alternating around the ring.
• Each C in cyclohexane has two different kinds of
hydrogens: (1) axial hydrogens are located above and
below the ring (along a perpendicular axis); (2) equatorial
hydrogens are located in the plane of the ring (around the
equator).
3 up C'a and 3 down C's [ Two kinds of H's

H + - axial

e=upC
equatorial ... H
# H. .
axiaJ ----. H
equatorial

0 = downC
• Axial bonds are oriented above and below.
• Equatorial bonds are oriented around the equator.
12

/
Cyclohexane
If a cyclohexane ring were flat.. ..

angle strain
Q ~
~'ti
})(_H tonlonal strain

120°
The internal bond
angle is >109.5°.
H"' AJI H's are aligned.

In reality, cyclohexane adopts a puckered " chair" conformation, which

is more stable than any possible other conformation.
The carbon skeleton of chair cyclohuw]

The chair conformation is so stable because it eliminates angle strain

(all C-C-C angles are 109.5°), and torsional strain (all hydrogens on
adjacent C atoms are staggered). H
109.5°
-{ All H's are staggered]
.__--.:
H 10

/
 Structure of Cyclohexane (C6H12).

In Chair form, there are six C-H

a a
bonds which are parallel to the
e axis of symmetry and they are
called axial bonds (denoted by a).

The remaining six C-H bonds are

e
directed at an angle of 109.5 deg
a to the axis of symmetry and they
a
are called equatorial bonds
Axis (denoted by e).
~
IEID>~IE!RlU
 Structure of Cyclohexane (C5H12).

Thus each carbon atom in the

a a
chair form will be attached to one
e axial and one equatorial bond, and
if we consider the adjacent C-H
bonds they are all staggered with
respect to each other. Thus the
e
chair form is free from torsional
a strain and bond opposition strain.
a

Axis
• An important conformational change in cyclohexane involves
" ring-flipping. " Ring-flipping is a two-step process.
• As a result of a ring flip, the up carbons become down carbons,
and the down carbons become up carbons.
• Axial and equatorial H atoms are also interconverted during a
ring-flip. Axial H atoms become equatorial H atoms, and
equatorial H atoms become axial H atoms.

An up C becomes a down C.

A down C flips up. I An up C flips down~

...
~ ...
chair boat 2nd chair
form form form
A down C becomes an up C. 15

/
 Structu re of Cycloh exane (C5H12).
~

1.8 Kcal
~ ~ ----- -----! _______________ _

11 Kcal
5.5 Kcal

---- ------------- ------------- ------- ------------- ------------- -----1

Chair Half Chair Twisted Boat Boat
IEID>~ll:IU
Conformations
The Conformations of Cyclohexane
and Their Energies

half-cha1ir ").
t=>~
half-chair
12.1 kcal/m
50.6 kJ/m
boat

twist- twist-
boat boat

5.3 kcal/m 6.8 kcal/m

22 kJ/m 28 kJ/m
chair chair
 J: C:.'fCJ.:OMJ!:::itANE5
..COl4.RJRN Jrr.ION& ::ir.

~~ !f: ~~~~ ln h d?diri CO~Nl'iYi~

~ Q ~ In! ~

Ex,.I;.- ~~ Q~
~ ~ -rm c:n, ~
Ill '\I.la~ pm!'-11:D5, r.
~o-~pos.~
M~ & dOWl'I ~Dn5 & houl :!5J· RJ~~ 4:n ~ Iii w ~ d ~ -

"Th
. J;A~, nth a_ti)r:1-i ~'fl a ~~ rt'fj NII . . , M a~;gl . ~ ~ ~ '-1,~
PP , Ead-. S'l"ll<P ~ br.. ~ 14~ M"' Cl ~ ~P·
D ! ~ ~Af!~T ~ Q.,i;O,I 6 tq,.~~ ~>ti.am ~ durira D'II ~ f'p, Lllhl'IE.
~ I .~ ~ ~! fJ
I• . U'