‫بسم هللا الرحمن‬

‫الرحيم‬
 Basic Principles
of
Organic Chemistry
Course outline & topics

 Introduction
Organic compounds
Types of covalent bonds
Classification of organic compounds

 Nomenclature, preparation and reactions of organic compounds

 Isomerism
 Introduction
• Organic compounds
Organ (human, animals or plants)

Friedrich Wohler

O

NH4 OCN H2N C NH2

Ammonium cyanate Urea

inorganic cpd organic cpd
 Organic Compounds:
• Definition:

“Organic compounds are defined as

compounds that contain carbon”.

• Tetravalent carbon H
H H
H C H C C
H H
H
 Types of carbon-carbon covalent bonds

covalent single bond covalent double bond covalent triple bond

c c c c c c
strong  bond one strong  bond one strong  bond
and one weak  bond and two weak  bonds

Saturated compounds
Unsaturated compounds
react by substitution react by addition
 Classification of Organic Compounds

Organic compounds

Hydrocarbons Derivatives
of hydrocarbons
(only C and H )

C and H with O, S, N,Si, Mg,...

Aliphatic HC Aromatic HC
OH Alcohols

CHO Aldehydes
Open chain Cyclic
(Acyclic) COOH Acids

NH2 Amines
Saturated Unsaturated Saturated Unsaturated
SH Thioalcols
(Alkanes)
(Cycloalkanes) (Cycloalkenes)
CH3-CH2-CH3
(Alkenes) (Alkynes)

CH3-CH=CH2 CH3-CC-H
ALKANES
 ALKANES

 They are aliphatic hydrocarbons with molecular formula

CnH2n+2 , Where n = 1,2,3,4…etc.

 *All carbon atoms in alkanes are sp3 hybrdized atom with

tetrahedral structure

+ 3 C

S P
SP3
(Tetrahedral structure)
 Alkanes
n CnH2n+2 Name

1 CH4 Methane

2 C 2H6 Ethane

3 C3H8 Propane

4 C4H10 Butane

5 C5H12 Pentane

6 C6H14 Hexane

7 C7H16 Heptane

8 C8H18 Octane

9 C9H20 Nonane

10 C10H22 Decane
 Nomenclature
1 ) Common names:
CH4 CH3 CH3 CH3 CH2 CH3

Methane Ethane Propane

• Notes:
* The prefix iso - is added to the compounds in which the second carbon atom in •
the carbon skeleton carries two methyl groups. CH
3
CH C
H3C

Iso-
* The prefix neo - is added to the compounds that carry three methyl groups at •

the end of the carbon chain. CH3

CH3 C C
CH3

Neo-
 C4H10
Butane

CH3
CH3 CH2 CH2 CH3 CH CH3
n-Butane CH3
C5H12
Pentane Iso-Butane

CH3 H3C
CH3 CH2 CH2 CH2 CH3 CH CH2 CH3
CH3 H3C C CH3
n-Pentane
H3C
Iso-Pentane
Neo-Pentane
 C6H14
Hexane

CH3
H3C
CH3 CH2 CH2 CH2 CH2 CH3 CH CH2 CH2 CH3
CH3 C CH2 CH3
n-Hexane CH3
Iso-Hexane
H3C
Neo-Hexane
 IUPAC NOMENCLATURE
 International
 Union of
 Pure and
 Applied
 Chemistry
2) IUPAC names
 Rules

1) The longest continuous carbon chain is taken as the

parent hydrocarbon (Base name).

8 CH3
CH 3
7 CH2
CH 2

CH3 6 CH2 CH 2
CH3

CH 3 CH CH 2 CH 2 CH CH3 CH3 CH CH2 CH 2 CH CH 3

1 2 3 4 5 1 2 3 4 5 6

octane not Hexane

2) The numbering of the parent hydrocarbon starts from the
end that gives the substituent the least possible numbers.

8 CH3 1 CH3
7 CH2 2 CH2
CH3 6 CH2 CH3 3 CH2
CH3 CH CH2 CH2 CH CH3 CH3 CH CH2 CH2 CH CH3
1 2 3 4 5 8 7 6 5 4

2,5-Dimethyloctane not 4,7-Dimethyloctane

3) When the parent hydrocarbon contains two or more of the
same substituent use the prefix di, tri, tetra…etc.
CH3

CH3 C CH2 CH2 Cl

CH3

1-Chloro-3,3-dimethylbutane

4) When the parent hydrocarbon contains two substituent at the

same position, the number is supplied for both (e.g. 3,3-dimethyl,
3-methyl-3-ethyl…etc.
CH2CH3

CH3CH2 C CH2 CH2 Cl

CH3

1-Chloro-3-ethyl-3-methylpentane
•Examples:
CH3 CH3 CH3 Cl
CH3 CH CH CH2 CH CH3 CH3 CH CH2 CH2 CH CH3
CH3 Cl
1 2 3 4 5 6 1 2 3 4 5 6

2,3,5-Trimethylhexane 2,5-Dicloro-2-methylhexane
 Types of carbon atoms.
Primary (1ry)
Primary (1ry) Secondary
(2ry) CH3 Secondary (2ry)
Secondary
Primary (1ry) CH2 Secondary (2ry)
(2ry)
CH3 CH2 Primary
(1ry)
CH3 CH CH2 CH2 C CH3

CH3
Quaternary
Tertiary
(4ry)
(3ry)
Primary
(1ry)
Methods of preparation of alkanes
1) From alkyl halides
a) Reduction using Zn/acetic acid

2H
R X R H + HX
(Zn/acetic acid)

2H
CH3CH2Br CH3CH3 + HBr
(Zn/acetic acid)
Bromoethane Ethane
 b) Through Grignard reagent

Mg H2O
R X R MgX R H + MgXOH
dry ether
Grignard reagent

(alkyl magnisum halide)

Mg H2O
CH3CH2Br CH3CH2MgBr CH3CH3 + MgXOH
dry ether
Bromoethane Ethyl magnisum bromide
c) Through Wurtz reaction

2 Na
2R X R R + 2 NaX

2 Na
2 CH3 Br CH3 CH3 + 2 NaBr
Bromomethane Ethane

2 Na
CH3 Br + CH3CH2Br CH3CH2CH3 + 2 NaBr

Bromomethane Bromoethane Propane

2) From sodium and potassium salts of
carboxylic acids
By decaboxylation using soda lime (NaOH/CaO)

NaOH/CaO
R-COONa R-H + Na2CO3

NaOH/CaO
CH3-COONa CH4 + Na2CO3
Sodium acetate

NaOH/CaO
CH3CH2-COONa CH3-CH3 + Na2CO3
3) By catalytic hydrogenation of unsaturated
hydrocarbons
H2/Ni H2/Ni
R CH CH2 R CH2 CH3 R C CH

Alkene Alkane Alkyne

H2/Ni H2/Ni
CH3 CH CH2 CH3 CH2 CH3 CH3 C CH

Propene Propane Propyne

Chemical Reactions
1) Halogenation: by substitution
CH4 + Cl2 heat
or h CH3Cl + HCl
Methane Chloromethane

Cl2

CH2Cl2 + HCl
Dichloromethane
Cl2

CHCl3 + HCl
Trichloromethane
Chloroform
Cl2

CCl4 + HCl
Tetrachloromethane
Carbon tetrachloride
2) Nitration
HNO3
CH4 o
CH3NO2 + H2O
400 C
Nitromethane

3) Oxidation

CH4 + 2 O2 CO2 + 2 H2O + Energy