Department of Chemistry

CHEM 3210 Stereochemistry Tutorial # 1

To be prepared for the week of January 25, 2021

1. Assign (R) and (S) designations to the stereocentres (if applicable) in the
compounds shown below and determine whether or not they will rotate
plane polarized light.
HO
OH Cl
H 3C CN
N Cl Ph
HO O
HO O
CH3 Ph OH H
OH Br
OH Cl
H3CO O
B C D E CH2OH

2. Identify how the following compounds are related to each other (e.g. identical,
enantiomers etc.) and assign (R) and (S) designations where applicable.
CH3
(i) H OH CH3 H3C OH

and
H OH
CH3 H OH H
CH3

CH3 H2C C H
(ii)
O

and

H C CH2 CH3

CH3

(iii) CH3 OH

HO H H 3C H
and
H Cl H 3C H

CH3 Cl

Cl H
Cl
(iv)
H Cl
and
Cl H
Br Br

H H
H
Br

H Br
(v)
C C C and H Cl

Cl H

(i) H
SH
H CH3
H
H3C CH3
and
HS CH3 H
SH HS

(ii)

Cl and

Cl
(iii)
CH2OCH3
HOH2C H
HO CHO OH
and HO
CHO CH2OCH3
H OH
CH2OH

CN
(iv) C(O)NH2
F3C C(O)NH2
NC CF3 and SH
H3CO SH
C(O)Cl Cl(O)C OCH3

(i) H3C H OH
H3C Cl
OH and
CH3 NH2
H NH2

H3C Cl

(ii)
CO2H H
Br
H Br
HO2C CH2
and C
C6H5 SH H
C6 H5
SH
CH
CH2

F CH3
(i)
CO2H
Br
H3C F
Br HO2C

(ii) H2N I H NH2

H3C H I CH3

(iii) Cl CH3
H Cl
H H H Br

Br H H
CH3

(iv) Cl
Cl H
H Cl
H Cl
H H
H H H

(v)
HO

OH

3. Draw and name all possible stereostructures (including geometric isomers) for
CH(Br)=C(CH3)C(F)=C(NH2)CH(OH)CH3.
 4. With the following molecules, determine if either (a) a plane of symmetry (b) an
axis of symmetry or (c) a rotation-reflection symmetry element exists.

H SO 3H
(a) (b) OH (c) (d) N
OH
NC
H H N
H
HOOC F HO
SO 3H

(e) (f) (g) OH

HO F

OH

WAG

Lecture # 2 Notes

Enantiomers – a pair of molecules which are non-superimposable mirror images of each

other.
A mixture containing a non-50:50 ratio of enantiomers is referred to as a scalemic
mixture.

Enantiomeric excess (e.e.) – provides a measure of the enantiomeric make up of a sample

containing both enantiomers.
% e.e. = No. of mol. of enantiomer A – No. of mol. of enantiomer B/ No. of mol of both
enantiomers x 100%.

Optical activity
Molecules that induce rotation of plane polarized light are said to be optically active.
- Rotation of plane polarized light to the right – dextrorotatory (d) [+]
- Rotation of plane polarized light to the left – laevorotatory (l) [-]
Specific rotation – the amount of rotation by 1.00 g of sample in 1.00 mL of solution in a
tube of path length of 1.00 dm at a specific temperature, wavelength and solvent.
[α]T = α / l (in dm) x c (in gcm-3) [Determined at a specific wavelength]
Optical purity – Determination of enantiomeric composition of a sample
% optical purity = [α]sample x 100/ [α]pure enantiomer

Symmetry
An object is said to possess a symmetry element if the corresponding symmetry operation
converts it into an object superimposable on the original.

A molecule has symmetry when certain parts of it can be interchanged with others
without altering either the identity or the orientation of the molecule. The interchangeable
parts are said to be equivalent to one another by symmetry.

Possible symmetry operations

a) Rotation through 360o x m/n where m is a positive integer< n about a
simple axis of symmetry of order n (symmetry element symbol: Cn).
b) Reflection in a plane of symmetry (σ). – Plane bisecting molecule so that
half of the molecule is the mirror image of the second half.
c) Inversion through a centre of symmetry (i) – all atoms are reflected through
a point in the molecule.
d) A combination of rotation and reflection about a rotation-reflection axis of
symmetry of order n (Sn).

Molecules which can be superimposed on their mirror images are achiral.

A molecule is achiral if it contains any of the symmetry elements Sn, i or σ.
Stereoisomerism in Medicine/ Agriculture

(R) – (+) Thalidomide – sedative, antinausea agent for use during early stages of
pregnancy.
(S) – (-) Thalidomide – causes high incidence of deformities in children.
O

N O

O O (R) or (S)?
H

(S)-(+)- α-(2-Bromophenoxy)-propionic acid – Plant growth stimulator.

(R) – (-)α-(2-Bromophenoxy)-propionic acid – Retards plant growth.
Br

H3C CO2H

O
H (R) or (S)?