CHE 1000

Lecture Notes

By Peter Mubanga Cheuka

University of Zambia, Department of Chemistry, P.O Box
32379 Lusaka Zambia
What Is Organic Chemistry Good For?

A common question that chemistry students often have:

“Why do I have to take organic chemistry, anyway?”

 Natural to wonder, particularly given that everybody

studying to be a chemist, biologist, or medical worker is
stuck taking it.

 Probably wondering whether this is just a conspiracy put

forth by the chemistry department to get more funding.
 CH3 CH3
H3C
C CH
H3C C CH3
H2
isooctane (2,3,5-trimethylpentane)
a major constituent of petrol volatile inflammable liquid
CH3
CH3
N CH3
HN

HO N Cl N

MeO Chloroquine – A highly effective

N
anti-malarial agent, a drug developed
from quinine
Quinine - an alkaloid first extracted from the bark of
the South American cinchona tree and used to treat
fevers, especially malaria.
Selected Esters That Are Used as Flavouring Agents
IUPAC Name Structural Formula Characteristic
O CH3 Flavour and Odour
Isobutyl methanoate H-C-O-CH2-CH-CH3 raspberry
O
propyl ethanoate pear
CH3-C-O-(CH2)2-CH3
O
pentyl ethanoate CH3-C-O-(CH2)4-CH3 banana
O
octyl ethanoate CH3-C-O-(CH2)7-CH3 orange
O
pentyl propanoate CH3-CH2-C-O-(CH2)4-CH3 apricot
O
methyl butanoate CH3-(CH2)2-C-O-CH3 apple
O
ethyl butanoate CH3-(CH2)2-C-O-CH2-CH3 pineapple
Some Anti-HIV Drugs
H
Ph S O N
OH H Me Me O H
O
HN N N HO
N O N N
H H
O H O Me OH
H
Ph Nelfinavir
Lopinavir O
Me
HN
O
O
N H HO H H NH
HO
N N
N H O
O H H OH
CONH2 H
N3
Sequinavir Zidovudine or
Azidothymidine (AZT)
A Word or Two from the Wise

How to Do Well in Organic Chemistry

1. Learn the vocabulary! If you want to understand this (or any other)
field, you need to understand the language being spoken. All the
memorization in the world does you no good if you don’t know what
people are asking you!

2. Keep up with your studying day to day –– never let yourself get
behind, or better still, be a little ahead of your instructor.

3. Slow and steady wins the race! Study materials in small units, and
be sure you understand each new section before you go on to the
next.
4. Work all of the in-chapter and assigned problems.

5. Write when you study. Write the structures, reactions, mechanisms,

and so on, over and over again. You need to know the material so
thoroughly that you can explain it to someone else. This level of
understanding comes to most of us through writing.

Only by writing the structures, reactions, mechanisms do we pay

sufficient attention to their details.

6. Learn by teaching and explaining. Study with your student peers

and practice explaining concepts, reactions, and reaction mechanisms to
each other.
7. Get people’s help only when you are completely stuck; the most
important thing is actually understanding how to get the right
answer.

The value of a problem is in solving it!

WORK as many problems as possible

Organic Chemistry is not a monster to be battled, rather it is it is a

challenge to be enjoyed and cherished….. RELISHED.

It really is not as hard as you think.

8. Don’t let other people scare you!
Organic chemistry gets a bad rap for being hard. Everybody has a best
friend who “became a philosophy major because they couldn’t pass
organic chemistry.”

Don’t let this bother you. Just because some people have trouble with
organic chemistry doesn’t mean you will. After all, you’ve got us to
guide you through it!
Introductory Organic Chemistry

About Organic Chemistry

❖ Organic chemistry is the study of carbon containing compounds.

❖ Organic compounds always contain carbon and hydrogen atoms.

❖ They can also contain other atoms e.g. O, N, S, F, Cl, Br, I etc.

❖ HETEROATOMS are any atoms, other than carbon or hydrogen, in

an organic compound.

❖ Organic compounds comprise > 98% of all known chemical

substances!
Systematic Nomenclature – IUPAC
Nomenclature
Introduction to Reaction Mechanisms
 Reactions of Alkanes
❖ Alkanes are saturated hydrocarbons with the general formula CnH2n+2
❖ They are obtained from crude oil by fractional distillation, cracking
and reformation.
❖ Alkanes are used as fuels.
Alkanes as Fuels
❖ A fuel releases heat energy when burnt.
Complete Combustion (In excess oxygen)

Incomplete Combustion (In limited oxygen)

❖ Compared to complete combustion, incomplete combustion produces

less energy per mole.
❖ The carbon (soot) from incomplete combustion can cause respiratory
problems and global dimming which is a reflection of the sun’s light.
❖ Carbon monoxide is an odourless but highly toxic gas.
❖ If it builds up in an enclosed space due to faulty heating appliances,
CO an cause death.
❖ The toxicity of CO is due to the strong bonds it forms with
haemoglobin in the red blood cells. Because this bond is stronger than
the one between oxygen and haemoglobin, CO prevents oxygen from
attaching to haemoglobin.
Pollution from Combustion
❖ Petroleum fractions also harbour sulfur-containing impurities which
produce SO2 when burnt.

❖ Because coal contains large amounts of sulfur, its use in power

stations results in the emission of large amounts of SO2. Once in the
atmosphere, SO2 dissolves in atmospheric water to produce acid rain.
❖ The reaction between N2 and O2 inside the car engine produces
nitrogen oxides (NOx).
❖ NO can form smog and is toxic. NO2 is toxic and forms acid rain.
❖ CO2 contributes towards global warming.
❖ Unburnt hydrocarbons also contribute to formation of smog.
Global Warming
❖ CO2, CH4, and water vapour (H2O) are all green house gases. They
trap the infra-red energy irradiated from the earth in the atmosphere.
❖ Water is the main greenhouse gas (but is natural), followed by carbon
dioxide and methane.
❖ In recent years, CO2 levels have risen substantially due to increased
burning of fossil fuels.
❖ CO2 is a particularly effective green house gas and its increase is
thought to be largely responsible for global warming.
❖ The Earth is thought to be getting warmer, and many scientists believe
it is due to increasing amounts of green house gases in the
atmosphere.
❖ Sustainable energy sources need to be developed. These could include
hydrogen-burning battery- and solar-powered cars.
❖ Other alternatives include cars run on methane, ethanol (produced by
the fermentation of sugar cane).
❖ In all these alternative fuels, one should consider the overall carbon
economy.
• What carbon emissions are released in the production of the
alternative fuel?
• How much carbon dioxide is released as it is burnt?
• How easy is it to refuel the vehicle?
• Is the process really carbon neutral?
❖ For instance, the fermentation of plant and animal waste produces
methane. CO2 is absorbed during the growth of the plants. The
fermentation of plants such as maize can produce ethanol too.
Therefore, the plants act as a carbon sink. But the energy needed for
producing these biofuels mean these alternatives may not be really
carbon neutral. Additionally, using too much land for fuel rather than
food production is not very attractive.
Free Radical Substitution Reaction of Alkanes
❖ Generally, because the C-C and C-H bonds in alkanes are relatively
strong, alkanes do not react with many reagents.

❖ In the presence of UV light, alkanes react with chlorine to form a

mixture of products with the halogens substituting hydrogen atoms.
Mechanism: Free Radical Subtsitution
Substitution reactions of Halogenoalkanes
Alkenes
Stereoisomerism in alkenes (Geometric isomerism)
❖ Stereoisomers have the same molecular and structural formula but
have a different spatial arrangement of atoms.
❖ Alkenes can exhibit a type of isomerism called E-Z stereoisomerism.
❖ E-Z stereoisomers can exist when:
• There is restricted rotation around the C=C double bond.
• There are two different groups/atoms attached at both double bond carbons.