Problem Set 4

(1) Using a chair structure, draw the most stable conformation of the substituted cyclohexane shown
below. Be sure that the axial and equatorial bonds are well illustrated.
H

CH3

CH3
CH3

C(CH3)3

H3C

(H3C)3C
H

is the same as

(2) Given the following partial structure, add a substituent X to C-1 so that it is gauche to C-3. Is
substituent X in the axial or equatorial position..
X
3
1

X is in the axial position

(3) Which is the more stable species and why?

OH

OH
HO

HO

and
HO

HO

OH

OH

OH

OH

ring 1

ring 2

OH
OH
OH

ring

OH
OH

HO

flip
OH

HO

OH

OH

ring 1
OH

OH
OH

ring
flip
OH

HO
HO

OH
OH
HO

OH

ring 2
Since ring 2 has one conformation whose substituents are all equatorial, ring 2 is more stable.

(4) Provide Newman projections for the most stable conformations of:
butane

1,2-dimethylcyclohexane

CH3

H3C

H3C

CH3

CH2

CH2
H

2-methylpropane
CH3
H

H3C

H
H

(5) D-glucose is a sugar metabolized by our bodies as a source of energy. It has a six-membered ring
with a structure similar to that of cyclohexane. It exists as two stereoisomers, referred to as alpha and
beta, shown below. Draw out the two chair forms of d-glucose and show which stereoisomer is more
stable sterically. (hint: the CH2OH group is always in the equatorial position.)
HOH2C

OH

OH

HO

HOH2C

OH

OH

HO
OH

OH

-d-glucose

-d-glucose
HOH2C
O

HOH2C
HO
HO

HO
HO
OH
OH

O
OH
OH

-d-glucose
-d-glucose
Since all of the OH groups are equatorial in the beta form, it is more stable.