Introduction

to Organic Chemistry
Stereochemistry – Problem Set


OH O
enantiomers
O OH

Me OH HO Me

A NH2 B NH2
diastereomers diastereomers diastereomers

OH O O OH

Me OH HO Me
C NH2 enantiomers D NH2


jonathan.burton@chem.ox.ac.uk

Introduction to Organic Chemistry – Stereochemistry Problem Set

Below you will find a set of problems related to the stereochemistry part of the course.

1. How would you predict in principle whether a molecular compound is chiral and can be resolved
into enantiomers?

2. Which of the following molecules are chiral?

Br Br Me
O
N N
Me
H H
Me Br O
Me Me

Cl Cl Cl Cl Cl Cl Cl Cl
• • • • • •
H H H H H H H H

OH O
HO OH HO OH
OH O

O O O O
S S
O Ph Ph Ph Me
O

3. a) Draw all the stereoisomers of the following molecules.

b) What are the relationships (e.g. enantiomers or diastereomers) between the
stereoisomers in each case?
c) Identify the meso forms and state which of the stereoisomers are chiral.
NOH OH
Me OH Me HO OH
PhN=N CH=CHPh
Me OH Me HO OH
OH

4. The following are different representations of the stereoisomers of cyclohexan-1,2-diol. What are
the relationships between the different representations? Are they the same, enantiomers or
diastereomers?

OH OH
OH
OH OH OH HO
HO
OH OH

Introduction to Organic Chemistry – Stereochemistry Problem Set

5. Using the Cahn-Ingold-Prelog sequence rule assign R or S, or E or Z, stereochemical descriptors to

all of the following molecules.

HSe HO
CF3 CO2H
Ph Cl O O
HO Cl HO
NH2
F O O HO
OH

The following problems can be attempted once you have covered a few more of the 1st year
organic chemistry courses

6. Racemisation is the conversion of one enantiomer (or an excess of one enantiomer) into a 50:50
mixture of enantiomers. To draw a mechanism for racemisation you need to be able to draw the
conversion of one enantiomer into the other enantiomer. Alternatively if you can draw a
mechanism which involves an intermediate that contains a plane of symmetry then the product will
be racemic.
The following compounds racemise under the conditions shown, provide a mechanism; the starting
materials are all enantiopure
OH
N
OMe
O
OH
H
Ph H
racemises-in-acid racemises-in-acid racemises-in-acid racemises-in-acid

O O O
Ph O OH
Ph O
OMe
Me Me

racemises-in-base racemises-in-acid racemises-in-base

7. The following reactions all yield racemic products provide explanations – the starting materials
are all enantiopure.

O O
NaOMe,2then
H PBr3 H MeI
Ph OH Ph Br
CO2Me MeO2C Me

acid

OH