Organic Chemistry

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Organic Chemistry
Organic chemistry may be defined as the chemistry of
carbon compounds. However, simple carbon-containing
compounds (such as carbon monoxides, carbon dioxide
and hydrogen cyanide) and carbon-containing salts (such
as carbonates and cyanides) are not generally considered
to be organic compounds. They are usually studied in
inorganic chemistry courses. Over 96% of known
chemical compounds contain carbon, these are known as
organic compounds
*Differences between Organic and Inorganic Compounds
Properties
*Structure
*solubility
Organic chemistry
In organic chemistry
*Contain carbon as the principle
*Study of compounds that do not
element
contain carbon as the principal element
*Contain carbon and Carbon-carbon or
*Usually do not contain carbon and
Carbon-Hydrogen covalent bonds
never contain carbon-carbon or carbonHydrogen covalent bonds.
*Usually dissolve in organic solvent
*Usually dissolve in water
*Boiling point
*low
*High
*Melting point
*low
*High
*chemical bond
*Covalent bond
*Ionic bond
1.Using the table below, check a compound is organic or inorganic.
(5 marks )
Compound
Organic Inorganic
Compound
Organic Inorganic

CO
CH4

CH3OH
NaHCO3
HCl
C6H12O6
NH3
Na2CO3
CO2
K2Cr2O7
CrS
Ca(OH2)
C2H4
Co(NO3)2
C4H10
C19H28O2
C8H18
CH3OCH3
Cu2O
C18H21NO3
Cr2O3
CH3COOH
CHCl3
CH3NHCH3


Chemical bond and valence
Valence : number of electron which place in highest
shell
Type of chemical bond
Ionic bond
Covalent bond
Ionic Bond
 Between atoms of metals and nonmetals with very different
electronegativity
 Bond formed by transfer of electrons.
 Examples; NaCl , CaCl2
1). Ionic bond – electron from Na is transferred to Cl, this
causes a charge imbalance in each atom. The Na becomes (Na+)
and the Cl becomes (Cl-), charged particles or ions.
COVALENT BOND
bond formed by the sharing of electrons
Covalent Bond
 Between nonmetallic elements of similar electronegativity.
 Formed by sharing electron pairs
 Examples; O2, CO2, C2H6, H2O, SiC
type of covalent bond
Signal covalent bond
triple covalent bond
double covalent bond
H
Ethane
ethene
C
C
Acetylene
H
Electron Configuration of Carbon
Why is CARBON so special?
 Atomic number = 6
 6 protons, 6 electrons
 1s2 2s2 2p2 electron structure
 Valence of 4 electrons
 Need 8 electrons to fill valence shell
 Form 4 bonds with other atoms
 Can combine with 1, 2, 3 or 4 other C atoms
 Single, double, triple bonds
 Each bond consists of 1 electron from carbon & 1
electron from bonding atom
Importance of carbon atom
1.
2.
3.
4.
5.
Basis for all life
Form stable covalent bonds to other carbon atom
Can form single ,double and triple bond
Long carbon chain can be produced
Will bond with many other element.
Carbon contain 2electron paired in first shell(No sharing
electron)
No sharing electron
1S2
Carbon contain 4 electron in Second shell
No sharing electron
2S2
Sharing electron
2P2
Carbon atom must contain 4 electron unpaired to formation 4bond
to become more stable this acure by hybridzation
Hybridization: over lab between orbital's of electron to
formation new orbital contain unpaired electron formation
more bond
Some compound contain signal bond
c bond
C
Some compound contain double bond
C
bond
bond
c
Some compound contain trible bond
H C C H
2 bond
C
bond
c
Type of hybridization
SP3 hybridization
SP2 hybridization
SP hybridization
H C C H
Ethane
Ethene
Acetylene
3
SP
Ethane
hybridization
Electron configuration of carbon
only two unpaired
electrons
should form s
bonds to only two
hydrogen atoms
Lead to hybridization
occur
Hybridization of atomic orbitals
Is overlap of the s and p orbital's occur in two steps
.
1
2p
excite one electron
2s
.
.
2
mix orbitals
2s
2p
1s
+
3P
=
SP3
H
bonds
H
bonds
.
.
bonds
.
.
bonds
. .C. .
H
H
2
SP
hybridization
Ethene
Hybridization of atomic orbitals
Is overlap of the s and p orbitals occur in TWO steps
2p
1
.
excite one electron
2s
.
2
mix orbitals
2s
2p
.
1s
+
2p
=
sp2
sp2 Orbital Hybridization
Π
2 sp2
c
c
σ
σ
H
σ
p
H
σ
σ
H
H
SP hybridization
Ethane
sp Hybridization
and Bonding in Acetylene
H C C H
Acetylene
Hybridization of atomic orbitals
Is overlap of the s and p orbitals occur in three steps
1
2p
.
excite one electron
2s
.
2
mix orbitals
2s
2p
1S
1P
.
SP
sp Orbital Hybridization
p
2 sp2
c
σ
H
σ
Π
c
Π
σ
H
Classification of organic chemistry by functional group
Hydrocarbon :
These compound which contain carbon and hydrogen
H
C
C
H
classification
hydrocarbon
Aliphatic
alkanes
Cyclo alkanes
Alkenes
Alkyenes
Aromatic
Benzene
The IUPAC Nomenclature of Alkanes
IUPAC "International Union of Pure and Applied
Chemistry" names
 The IUPAC system is based upon a series of rules
which enable us to explain the structure of a compound
from its name.
We should start by learning the names of 10 simplest
straight chain alkanes.
i- Locate the longest continuous chain of carbon atoms
ii- Indicate the position of a side chain(replacement group) by
the lowest possible number.
replacement group
5
4
3
1
2
3
2
4
1
5
√
x
replacement group may be alkyl group or another atom(Halogen)
alkyl group) contain from hydrogen atom removed from alkane
CH4 –H ( Methane)  CH3- = (methyl )
CH3CH3 ( ethane )
CH3CH2- = ethyl
CH3CH2CH3 (Propane)CH3CH2CH2- = Propyl
Replace ane from alkane to yl
The substituent groups are listed
alphabetically
When two or more substituents are identical, indicate
this by the use of the prefixes di-, tri-, tetra-, and
so on.
Physical Properties of
alkane
Non
polar molecule
No soluble in water
Low melting point
Low boiling point
first four members (C1–C4 )are gases
C5-C17are liquids and above C17 are solid
Chemical Properties of alkane
Preparation of alkane
Hydrogenation of alkanes:
Reduction of alkyl haled
1-hydrolysis Girgnard reagent
R-X +Mg RMgX +H2O R-H
CH3CL + MgCH3MgCL+H2OCH4
Reduction by metal and acid
R-X +Zn+ H+ R-H+Zn+2+XCH3CH2CL +Zn+2+H+CH3CH3+Zn+2+XReaction of alkane
HALOGENATION
CH3 –CH-CH3
CH3
ISO BUTANE
CL2
CH3
CH3 –CH-CH2CL
ISO BUTYL CHLORIDE
+
CL
CH3 –CH-CH3
CH3
TERT BUTYLCHLORIDE
Reduction by metal and acid
Reaction of alkane
HALOGENATION
CH3 –CH2-CH3
Propane
Br2
CH3 –CH2-CH2Br
1Bromo Propane
+
Br
CH3 –CH-CH3
2Bromo Propane
.
Alkenes are unsaturated hydrocarbon, they contain a carbon-carbon double
bond which general formula .
Nomenclature:
 Count the number of carbon atoms in the longest continuous
carbon chain containing the double bond
 Change the ending from –ane by –ene
 Indicate the position of the double bond by the lowest possible
number
CH2 = CH - CH2 - CH3
1butene
CH3CH=CHCH3
2 butene
Alkynes
Alkynes contain a carbon-carbon triple bond, these compounds they have
the general formula CnH2n-2
Nomenclature:
 Count the number of carbon atoms in the longest continuous
carbon chain containing the triple bond
 Change the ending from –ane by –yne
 Indicate the position of the triple bond by the lowest possible
number
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