Introduction To Organic Chemistry

Lecture 1 12.1 Introduction

Learning Outcomes:
At the end of the lesson the students should be able to : 1. List the elements that made up organic compounds C, H, O, N, P, S and halogens. 2. State the ability of carbon to form 4 covalent bonds with other carbons or elements. 3. Differentiate between saturated and unsaturated organic compounds. 4. Give examples of organic compounds used in medicine, engineering, biotechnology and agriculture.

WHAT IS ORGANIC CHEMISTRY?

Organic chemistry is the chemistry of carbon compounds. Organic compounds contain H as well as C, while other common elements are O, N, the halogens, S and P. There are many varieties of organic compounds ( more than 10 millions!!!) They may exist as simple or complex molecules; as gases, liquids or solid and coloured or colourless.

 Examples :-

CH4
methane (a component of natural gas)

OCOCH3 COOH
methyl salicylic acid (aspirin-a drug)

O CH2 C NH O N S

penicillin (an antibiotic) COOH

Cl CH CCl3 Cl

dichlorodiphenyltrichloroetane (DDT- a pesticide component)

All organic compounds consist of carbon atom. Properties of carbon atom: -has 4 valence electrons. -can form 4 covalent bonds.
C C C C C C

Single bond

Double bond

Triple bond

Hydrocarbons

saturated

unsaturated
Contains at least one carbon-carbon double bond (-C=C-) or triple bond (-C C-). Examples: alkenes, alkynes.

Contains only single bonds ( -C-C- ) Examples: alkanes,

cycloalkanes

Uses of organic compounds

Medicine Antibiotics are used to fight bacterial and fungal infections Engineering Gasoline-as a fuel for internal combustion engines. Biotechnolo Genetic information like gy DNA Agriculture DDT-as insectisides to kill

Learning Outcomes:

Lecture 2: 12.2 Molecular and Structural Formulae

At the end of the lesson the students should be able to : Define structural formula. Draw structural formula in the form of expanded, condensed and skeletal structures based on the molecular formula. Explain primary (1), secondary (2), tertiary (3) and quaternary (4) carbon.

 Structural formula shows how the atoms in a molecule are bonded to each other. 3 types of structural formula:
condensed structure expanded structure skeletal structure

2- Dimensional formula

Condensed Structure
Does not show single bonds between carbon and hydrogen atoms, but double and triple bonds are shown. All atoms that are attached to a carbon are written immediately after that carbon.
C4H9Cl CH3CHClCH2CH3 (Condensed structure) CH3CH=CHCH3 (Condensed structure)

C4H8

Examples:
ii) Cyclohexane, C6H12 H2 C H2C CH2 iii) Aldehyde, CH3CHO H2C CH2 C O H2
CH3CH

Expanded Structure
Expanded structures indicate how atoms are attached to each other but are not representations of the actual shapes of the molecules.
H H C H H C C H

C4H9Cl
Molecular Formula

C H

Cl

Expanded structure

 Examples:
i) Alcohol (C2H6O)
H

H C H

H C H OH

ii) Carboxylic acid (C3H6O2 )

H H C H H C H O C OH

Skeletal Structure
Shows only the carbon skeleton. Hydrogen atoms are not written. Other atoms such as O, Cl, N etc. are shown. i) CH3CH(Cl)CH2CH3 =

Cl

H2C ii) H2C

CH 2 CH 2

Question
Expanded Structure Condensed Structure Skeletal Structure

CH3(CH2)CCl(CH3)
2

H H H H

CH3 C C CH CH3

3- Dimensional formula ( wedge dashed wedge line formula )

Describes how the atoms of a molecule are arranged in space.

Example : Bromomethane
Br C H H H

Br C H H H

H C H Br
or H

H C Br H

or H

Indication ::bonds that lie in the plane :bonds that lie behind the plane :bonds that project out of the plane

Classification of C atoms:
A carbon atom can be classified as primary carbon (1o) bonded to 1 C secondary carbon (2o) bonded to 2 C tertiary carbon (3o) bonded to 3 C quarternary carbon (4o) bonded to 4C

Example:
1. The classification of carbon atoms

Exercise:
How many a) 2 C atoms b) 3o C atoms c) 4o C atoms d) 1o H atoms are present ?

Answer:
a) 3 atoms b) 3 atoms c) 1 atom d) 15 atoms

Example:
3. The classification of alcohol 4. The classification of haloalkanes 5. The classification of amines

11.3 FUNCTIONAL GROUPS AND HOMOLOGOUS SERIES

Functional group is an atom or a group of atoms that determines the chemical properties of a organic compound. Why functional groups are important? Functional groups are important for three reasons: They are the units by which we divide organic compounds into classes. They are sites of chemical reaction; a particular functional group, in whatever compound it is found, undergoes the same types of chemical reactions. Functional groups serve as a basic for naming organic compounds.

 Homologous are compounds belonging to the same homologous series A homologous series is a functional group of compounds of similar structures and properties with the same functional group.

Some important functional groups in organic compounds :IUPAC nomenculatur e prefix- suffix -ane -ene -yne

Homologou s Series

Functional group

General Formula

Example

Alkane Alkene Alkyne

none C=C (double bond) CC (triple bond)

CnH2n+2 CnH2n CnH2n-2

CH4 Methane CH2 = CH2 Ethene CH CH Ethyne

CH3

Arene

CnH2n-6

-benzene Methylbenzene

(aromatic ring)

Alcohol

OH (hydroxyl) OR (alkoxy) X (halogen)

O

CnH2n+1 OH CnH2n+2O

Alkanol

CH3CH2OH Ethanol CH3OCH3 Methoxymethane CH3CH2Cl Chloroethane CH3C=O H Ethanal CH3C=O CH3 Propanone

Ether Haloalkan e

Alkoxyalkane

CnH2n+1X

Haloalkane

Aldehyde

CnH2nO

Alkanal

(carbonyl)
O

Ketone

CnH2nO

Alkanone

(carbonyl)

Carboxylic acid

O C OH

CnH2nO2

Alkanoic acid

(carboxyl) Acyl halide

O

CH3C=O OH Ethanoic acid

X C Cl (acyl)
O

CnH2n+1 COCl

Alkanoyl chloride

CH3C=O Cl Ethanoyl chloride

CH3COOCH3 Ethyl ethanoate

Ester

C O C (ester)
O

CnH2nO2

Alkyl alkanoate

Amide

NH2

CnH2n+1 CONH2 CnH2n+1 NH2

- amide

CH3CONH2 Ethanamide CH3NH2 Methanamine

(amide) Amine -NH2 (amino) - amine

Exercise 1:

Exercise 2:

Exercise 3: Determine the functional groups of each structures

Alkoxy
R O R`

Amino Carboxyl Hydroxyl Carbonyl

RN

O R C OH

R OH

R=O

Exercise 4:
Describe the functional groups in the following structures 1. 2.

3.

4.

Acyl chloride

Exercise 5: Label the functional groups in the following structures

1.

2.

3.

Exercise 6:
Classify the following compounds into their respective families

1.

2.

3.