SCH 102

SCH 102
Introduction to Organic Chemistry,
Chemistry of Alkanes and Cycloalkanes

Dr. Solomon Derese 1

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Dr. Solomon Derese; Chemistry Department
Room 118; [email protected]

Monday 8-10 am, MH1, A

Teaching timetable
Wednesday 8-10 am, MH1, B
PRACTICALS (15 marks)
Course Evaluation Two CATS (15 MARKS)
Final Exam (70 MARKS)
Recommended text books
1. Organic Chemistry, John McMurry
2. Organic Chemistry, Francis Carry
3. Organic Chemistry, Solomons T.W.G.
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Course Outline
1. Introduction to Organic Chemistry.
2. Atomic Structure, Chemical Bonding, Chemical
Structure and in Organic Compounds: Lewis
structure, resonance and hybridization.
3. Polar covalent bonds: electronegativity, dipole
moment
4. Overview of the Intramolecular and Intermolecular
Forces of attractions in Organic Molecules.
5. Overview of Types of Organic Reactions.
6. Basic Concepts of Organic Reaction Mechanisms.
7. Alkanes: Nomenclature, Structural Isomers,
Conformational Isomers and Reactions.
8. Cycloalkanes: Nomenclature, Conformational
Analysis and Reactions.
9. Overview of Stereochemistry.
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Success Depends
on the Second
Letter
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Introduction to Organic Chemistry

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What is organic chemistry?

Organic chemistry is the study of the chemistry of
carbon compounds.
The compounds of carbon are the central
substances of which all living things on this planet
are made.
Every living organism is made of organic chemicals.
The proteins that make up your hair, skin, and
muscles; the DNA that controls your genetic
heritage; the foods that nourish you; and the
medicines that heal you are all organic chemicals.
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Examples of Organic Compounds
CH4 DNA
Methane
(Chief constituent of natural gas)

O
Acetylsalicylic acid
OH (Aspirin)
(Pain reliever)
O

H O
R
NH2 OH
Aminoacids
(The building blocks of proteins)
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DEET, the active ingredient in the most widely used

insect repellents, is effective against mosquitoes,
fleas, and ticks.
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Polyethylene

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Although carbon is the principal element in organic
compounds, most also contain hydrogen, and many
contain nitrogen, oxygen, phosphorous, sulfur,
halogens or other compounds.
Example

Saflufenacil (Herbicide)
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Anyone with a curiosity about life

and living things, and anyone who
wants to be a part of the remarkable
advances now occurring in medicine
and the biological sciences, must first
understand organic chemistry.

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Although carbon is the principal element in

organic compounds, most also contain
hydrogen, and many contain nitrogen, oxygen,
phosphorous, sulfur, halogens or other
compounds.
Currently there are close to 37 million known
chemical compounds, of these 99% of them
contain carbon.

What makes carbon special?

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The reason for this are:
• As a group 4A element (at the centre of the
periodic table), carbon can share four valence
electrons and form four strong covalent bonds.
• Furthermore, carbon atoms can bond to one
another, forming long chains and rings from
the simplest methane with one carbon complex
molecules such as DNA with more than 100
million carbons.

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Carbon atoms can attach themselves to one another

to an extent not possible for atoms of any other
elements.
O

NH2

Each arrangement corresponds to a different

compound, and has it own characteristic set of
physical and chemical properties.
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Atomic mass

12
6 C
Atomic number
Electronic configuration: 1s22s22p2
2
1S 2S
2 2P 2
Ground state
px py p z
Carbon has four electrons in its outer most shell and
requires four more electrons in a covalent bond to
have a complete outer shell of electrons.
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Bond formation in carbon

1. Carbon is tetravalent; that is it forms four bonds

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2. A carbon atom can use one or more of its

valence electrons to form bonds with other
carbon atoms.

Single bond

Double bond

C C Triple bond
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Functional Groups
• Chemists have learned through many years of
experience that organic compounds can be
classified according to their structural features
and that members of a given family often have
similar physical and chemical behaviour.
• The structural features that make it possible for
classify organic compounds by reactivity are
called functional groups.

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A functional group is part of a molecule where most

of its chemical reactions occur. It is the part that
effectively the compound’s chemical properties (and
most of its physical properties as well).

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The chemistry of every

molecule, regardless of
size and complexity, is
determined by the
functional group it
contains.
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Alkanes
• They contain only C-C single bonds.
• The alkanes are the simplest class of organic
molecules because they contain no functional
groups. They are extremely unreactive.

Butane 3-Methylhexane Cyclohexane

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Alkenes
• Sometimes called olefins are hydrocarbons
which contain C=C double bonds.

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Alkynes
Alkynes are hydrocarbons that contain C≡C triple
bond.

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Aromatic
Compounds that contain benzene.

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Alkyl Halides
Contain an alkyl group bonded to F, Cl, Br or I.

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Alcohols

Alcohols contain a hydroxyl (OH) group.

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Ethers
Ethers contain R1–O–R2. It refers to any compound
that has two alkyl groups linked through an oxygen
atom.

R1-O-R2
O

Ethyl methyl ether

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Amines
Amines contain the amino (NR1R2R3) group, a
nitrogen attached to an alkyl group.

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Alhdeydes and Ketones
Aldehydes (R–CHO) and ketones (R1–CO–R2) contain
the carbonyl group C=O.

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Carboxylic Acids
Carboxylic acids (R–CO2H) contain the carboxyl group
CO2H.

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Esters
Esters (R1–CO2-R2) contain a carboxyl group with an
extra alkyl group (-CO2R).

R2
R1 O

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Commercial applications of esters
The characteristics fruity smell of esters lead to
their use in artificial fruit essences.
O O

O O

Methyl 3-methylbutanoate Propyl propionate

O O

O O
Butyl acetate 3-Methylbutyl acetate

O O

O O

Methyl octanoate Benzyl butanoate

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Amides
Amides (RCONR1R2)

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Acid Chlorides

Acid chlorides (R–COCl)

O

Cl
Acetyl chloride

Cl
3-Methylbutanoyl chloride
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Alkyl halide

Aromatic
Alkyl halide

Amide

Aromatic
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Application of Organic Chemistry in Drug

Discovery – a Case of the Anticancer Drug
Imatinib

Imatinib marketed as Gleevec/Glivec

IUPAC Name
N-(4-Methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)-
4-((4-methylpiperazin-1-yl)methyl)benzamide
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• Imatinib is used for the treatment of Chronic

Myelogenous Leukemia (CML), before its discovery
a diagnosis of a relatively uncommon cancer of the
blood and bone marrow, was a death sentence.
• Imatinib was discovered through collaboration of,
an oncologist, Brian Drucker, and a biochemist,
Nicholas Lydon, using results on the genetic basis
of CML.

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Genetic Basis of CML

CML is caused by the mutated chromosome bcr-abl.

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A number organic compounds were screened for

their ability to inhibit bcr–abl, and this resulted in
the discovery of imatinib as the drug of choice for
treatment of CML.

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Inhibition of bcr-abl by imatinib 45
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Overall survival on First-Line Imatinib

treatment of patients diagnosed with CML

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In this unit and subsequent organic chemistry units

you will learn about:

• Structure
• Nomenclature
• Properties
• Reactions
• Synthesis/Preparation

of such type of organic compounds.

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