1 2 3 4

H3C C C CH3 H
H2 H2 H
H H
butane ---->>> rotate with C3-C4 bond.

H H
H H

H H H H H H
H HH H H
H
Fully eclipse Gauche Eclipse Anti
Has more Has No Torsional Has Less Has No Torsional
Torsional strain strain, but there is Torsional strain strain and there is no
a steric strain by streric strain by alkyl
two proximal methyl groups (which are far apart)
groups.

Stability = Anti > Gauche > Eclipsed > Fully eclipsed

CH3
1 2 3 4 5 6
H3C C C C C CH3 H
H H2 H2 H2 H
H H
2-methylhexane ---->>> rotate with C3-C4 bond.

H H
H H

H H H H H H
H HH H H
H
Fully eclipse Gauche Eclipse Anti
Has more Has No Torsional Has Less Has No Torsional
Torsional strain strain, but there is Torsional strain strain and there is no
an electron repulsion electron repulsion
between two alkyl between two alkyl
groups (which are nearby) groups (which are far away)

Stability = Anti > Gauche > Eclipsed > Fully eclipsed

 CH3 CH3
1 2 3 4
H3C C C CH3 H
H H H

2,3-dimethyl butane ---->>> rotate with C2-C3 bond.

H H
H

H H H H
H

Fully eclipse Gauche Eclipse Anti

Has more Has No Torsional Has Less Has No Torsional
Torsional & strain, but there are Torsional & strain and has little streric strain
steric strains a steric strains by steric strains but alkyl groupsare opposite.
4 proximal methyl
groups.

Stability = Anti > Gauche > Eclipsed > Fully eclipsed

Obtain the missing conformer after 180o rotation for A and B. Also, predict which is more stable
from each case. Also, show the name of each alkane.

H H
H
180o H
H H
rotation
H H
H H n-pentane
H H
180o (Clock-wise)

180o (Clock-wise)

H H H H
180o
H rotation H
H H H
H H
H
n-pentane

Fully Exclipsed Anti (More stable)

(it has torsional & steric strains) (it has no torsional & steric strains)
11) (I) From the Newman projection of two different alkane conformations, draw all possible staggered forms and
circle the rotation angle (i.e. torsion or dihedral angle) that corresponds to the conformation. Also, name all
conformers and show the most stable form.

(-) counter clock-wise rotation Use back-group (+) clock-wise rotation

-60o -120o -180o -240o -300o -360o for rotation +60o +120o +180o +240o +300o +360o
(A) H
H

Skew

(B)
Br

Br

Eclipse

(II) Below, obtain the IUPAC name for the compound from both conformations (A & B).

A: B:

Nature of “axial” and equatorial" substituents in two different chair forms of

cyclohexane
 R
1

2'
R
2
R R
R
R
R R
2'
R
2

R R
3'
R
3 R

3'

3 R
R
R R

R
4

R
R
R
4
 more stable
(it has less 1,3-diaxial interaction)

up
down

more stable
(it has less 1,3-diaxial interaction)

H H H
H
H H
H
H H
H

1,3-diaxial interaction => this interaction destabilizes the axially-substituted

chair form of any cyclohexane - i.e. interaction between "two axial Hs and
"alkyl group". Also, there is a possibility of having an interaction between
"two alkyl groups" and this is called "steric interaction" which will still lead
to much higher energy conformation.
 ax & eq eq & ax

CIS
CIS

up
eq & ax down ax & eq
up
equally stable althoough there is a down
1,3-diaxial interaction via one axial-Me equally stable althoough there is a
1,3-diaxial interaction via one axial-Me
1,2-dimethyl
ax & ax
cyclohexane eq & eq
TRANS
TRANS

up down
eq & eq
ax & ax

down up
eq-eq combination is more stable, eq-eq combination is more stable,
because the conformation has no because the conformation has no
1,3-diaxial interaction 1,3-diaxial interaction

ax & ax eq & eq
CIS
CIS
down
up
eq & eq ax & ax
down
up

eq-eq combination is more stable, eq-eq combination is more stable,

because the conformation has no because the conformation has no
1,3-dimethyl 1,3-diaxial interaction 1,3-diaxial interaction
cyclohexane
ax & eq eq & ax
TRANS
TRANS

up eq & ax down
ax & eq

down up
equally stable althoough there is a equally stable althoough there is a
1,3-diaxial interaction via one axial-Me 1,3-diaxial interaction via one axial-Me
 ax & eq eq & ax

CIS
CIS

up
eq & ax down
ax & eq
up
down
equally stable althoough there is a
1,4-dimethyl 1,3-diaxial interaction via one axial-Me equally stable althoough there is a
1,3-diaxial interaction via one axial-Me
cyclohexane
ax & ax
eq & eq
TRANS
TRANS

up down
eq & eq ax & ax

down up
eq-eq combination is more stable, eq-eq combination is more stable,
because the conformation has no because the conformation has no
1,3-diaxial interaction 1,3-diaxial interaction