Department of

Pharmacy
PHARMACEUTICAL ORGANIC
CHEMISTRY-III
21PY2217T
Topic:

GEOMETRICAL ISOMERISM

Session - 1
CREATED BY K. VICTOR BABU
 AIM OF THE SESSION

To familiarize students with the basic concept of geometrical isomerism and stereochemical reactions

INSTRUCTIONAL OBJECTIVES

This Session is designed to:

1. To understand the concept of geometrical isomerism
2. To assign configuration for chiral molecules

LEARNING OUTCOMES

At the end of this session, you should be able to:

1. Define the terms cis and trans isomers, Z and E isomers
2. Explain the conformational isomerism in aliphatic and alicyclic compounds
3. Outline the stereo isomerism in biphenyl compounds
4. Summarize stereospecific and stereoselective reactions

CREATED BY K. VICTOR BABU

 SESSION INTRODUCTION

• In general, isomers contain double bonds, which cannot rotate (Rotation of bonds
is greatly restricted).
• The type of stereoisomerism, having two differently substituted atoms attached to
each other by means of double bond.
• Also known as
• geometric isomerism,
• configuration isomerism,
• Cis-Trans Isomerism or
• E/Z isomerism.
• The terms cis and trans are from Latin,
• Cis means "on the same side" and
• trans means "on the other side" or "across".

CREATED BY K. VICTOR BABU

CREATED BY K. VICTOR BABU
CREATED BY K. VICTOR BABU
CREATED BY K. VICTOR BABU
CREATED BY K. VICTOR BABU
 Three possible suggestions for remembering E and Z
• E: German word entgegen meaning against
• Z: German word Zusammen meaning together
• E is for "Enemies", which are on opposite sides.
• You don't, of course, need a way of remembering the Z as well.
• In Z isomers, the higher priority groups are on zee zame zide.
• It relies on the fact that the shapes of E and Z isomers are the opposite of the
shapes of the letters E and Z.
• In the letter E,
• the horizontal strokes are all on the same side;
• in the E isomer, the higher priority groups are on opposite sides.
• In the letter Z,
• the horizontal strokes are on opposite sides; in the Z isomer,
CREATED BY K. VICTOR BABU
CREATED BY K. VICTOR BABU
CREATED BY K. VICTOR BABU
CREATED BY K. VICTOR BABU
 SELF-ASSESSMENT QUESTIONS

1. Which of the following statement is true about racemic compounds?

a) They are a pair of enantiomers with equal amount

b) They cannot be isolated using any resolution process
c) The numeric value is obtained as optical rotation for racemates
d) Racemic compounds are a special class of chiral compounds

2. 2-butanol is optically active because it contains

(a) Chiral carbon

(b) Plane of symmetry
(c) Hydroxyl group
(d) Centre of symmetry

CREATED BY K. VICTOR BABU

 TERMINAL QUESTIONS

1. Define the terms cis and trans isomers, Z and E isomers

2. Explain the conformational isomerism in aliphatic and alicyclic compounds
3. Outline the stereo isomerism in biphenyl compounds
4. Summarize stereospecific and stereoselective reactions

CREATED BY K. VICTOR BABU

 REFERENCES FOR FURTHER LEARNING OF THE SESSION

Reference Books:
1. Stereochemistry by P.S. Kalsi
2. Organic Chemistry by Morrison and Boyd
3. Heterocyclic Chemistry by Raj K. Bansal
4. Organic Reactions and Mechanisms by O.P. Agarwaal
Sites and Web links:
5. Stereochemistry Defined (cliffsnotes.com)
6. 9.1: Some Important Concepts in Stereochemistry - Chemistry LibreTexts

CREATED BY K. VICTOR BABU

 THANK YOU

Team – Pharmaceutical Organic Chemistry-III

CREATED BY K. VICTOR BABU