26/09/2016
Organic Chemistry
Organic Chemistry
Organic chemistry is the chemistry of carbon. The
name “organic” reflect the fact that organic molecules
are derived from living organisms.
Why organic chemistry ?
we can find organic compounds everywhere around us
(foods, flavours, fragrances, medicines, toiletries,
cosmetics, plastic, paints, our body, and etc.).
Of the 10 million or so compounds that are known today,
about 9 million of those are carbon containing compounds
OM2029 1
26/09/2016
Organic Compounds
Typical organic compounds
(Properties):
• Contain carbon
• Have covalent bonds
• Have low melting points
C3H8
• Have low boiling points Propane
• Are flammable
• Are soluble in nonpolar solvents
• May be gases, liquids or solids
– Carbon: normally forms four covalent bonds.
C
H O H O
– Hydrogen: forms one covalent bond
H C C O H H HC C O H
H H
Some familiar organic compounds:
H H H H
H C H H C C C H
H H H H
Methane, CH4 Propane, C3H8
OM2029 2
26/09/2016
Hydrocarbons
Hydrocarbons C +H
Large family of organic compounds
Composed of only carbon and hydrogen
Saturated hydrocarbons Unsaturated hydrocarbons
Alkanes Alkenes, Alkynes
H & Aromatics
H C H
C C
C-C C=C C C
C C
H C H
H
Saturated in this context means that each carbon AinKek
theulé
hydrocarbon
structure Ahas
Kekuthe
lé structu re
maximum number of hydrogen atoms bonded to it.show ing all atoms as a line-angle formula
Classes of Hydrocarbons: Definition
Alkanes are saturated hydrocarbons with only carbon-carbon single
bonds. General formula for an alkane is CnH2n+2.. The suffix is“-ane”.
Ex: CH4 Methane, C2H6 Ethane, C3H8 Propane, C4H10 Butane
Alkenes are unsaturated hydrocarbons with at least one carbon-carbon
double bond. General formula for an alkene is CnH2n. The suffix is“-ene”.
Ex: C2H4 Ethene, C3H6 Propene, C4H8 Butene
Alkynes are unsaturated hydrocarbons with at least one carbon-carbon
triple bond. General formula for an alkene is CnH2n-2. The suffix is“-yne”.
Ex: C2H2 Ethyne(acetylene), C3H4 Propyne, C4H6 Butyne
(n is the number of carbon atoms)
OM2029 3
26/09/2016
Functional groups
An atom or group of atoms within a molecule that shows a characteristic set
of predictable physical and chemical properties.
The general formula is RX. R is called an alkyl group and. the X part of the
molecule is called the functional group. This functional group determines
many of the characteristic properties of members of the series.
Other alkyl groups include :methyl CH3, ethyl C2H5 ,propyl C3H7 and so on
– A way to classify families of organic compounds.
– They determine the chemical and physical properties of a molecule.
CH3
– They undergo the same types of chemical reactions.
CH3- CH- CH2- CH3
1 2 3 4
– A way to name organic compounds.
2-Methylbutane
Alkanes
(Paraffins)
OM2029 4
26/09/2016
Alkanes
CnH2n+2 n: number of carbon atoms
Methane
Tetrahedral
Expanded structural formula:
showing each bond line.
Molecular formula CH4 E.g. n = 1 CH4; n = 2 C2H6, etc
OM2029 5
26/09/2016
Ethane
C2H6 Molecular formula
Expanded structural formula
Condensed structural formula: with each carbon atom and
CH3 – CH3
its attached hydrogen atoms.
Naming of Alkanes
The molecular formula indicates just the number of each atoms in the molecule,
whereas the structural formula indicates how these atoms are arranged.
Prefix + ane CnH2n+2
OM2029 6
26/09/2016
Naming Substituents
International Union of Pure and Applied Chemistry (IUPAC)
In the IUPAC system:
• Removing a H from an
alkane is called alkyl
group.
-ane -yl
• Halogen atoms are
named as Flouride (F),
Chloride (Cl), bromide
(Br), Iodide (I)
OM2029 7
26/09/2016
Give the name of: CH3
CH3─CH─CH2─CH3
STEP 1 Longest chain is butane.
STEP 2 Number chain. CH3
CH3─CH─CH─CH3
1 2 3 4
STEP 3 Locate substituents and name.
2-Methylbutane
Give the name of: CH3 CH3
CH3─CH─CH─CH3
STEP 1 Longest chain is butane.
STEP 2 Number chain. CH3 CH3
CH3─CH─CH─CH3
1 2 3 4
STEP 3 Locate substituents and name.
2,3-dimethylbutane
OM2029 8
26/09/2016
Cl CH3
CH3─CH2─CH─CH─CH3
STEP 1 Longest chain is pentane.
STEP 2 Number chain from end nearest substituent.
Cl CH3
CH3─CH2─CH─CH─CH3
5 4 3 2 1
STEP 3 Locate substituents and name alphabetically.
3-chloro-2-methylpentane
CH3 CH3
| |
CH3─CH─CH2 ─CH─CH3 2,4-dimethylpentane
1 2 3 4 5
Cl CH3
| |
CH3─CH2─CH─CH2─C─CH2─CH3
|
Cl
7 6 5 4 3 2 1
3,5-dichloro-3-methylheptane
OM2029 9
26/09/2016
Br
CH3─CH─CH2─CH2─Cl
STEP 1 Longest chain has 4 carbon atoms.
C─C─C─C
STEP 2 Number chain and add substituents.
Br
C ─ C ─ C ─ C ─ Cl
1 2 3 4
STEP 3 Add hydrogen to complete 4 bonds to each C.
Br
CH3─CH─CH2─CH2─Cl 2-bromo-4-chlorobutane
Isomers
• Have the same molecular formula.
• Have different atom arrangements (different structural formula).
CH3CH2CH2CH3
Butane
C4H10
CH3
2-Methylpropane
C4H10 CH3CHCH3
OM2029 10
26/09/2016
Physical Properties of Alkanes
• Nonpolar
• Insoluble in water.
• Lower density than water.
• Low boiling and melting points.
• Gases with 1-4 carbon atoms.
(methane, propane, butane)
• Liquids with 5-17 carbon atoms.
(kerosene, diesel, and jet fuels)
• Solids with 18 or more carbon atoms.
(wax, paraffin, Vaseline)
Boiling & melting points of Alkanes
Number of carbon atoms ↑ bp & mp ↑
Number of branches ↑ bp & mp ↓
CH3
CH3CH2CH2CH3
CH3CHCH3
OM2029 11
26/09/2016
Chemical reactions of Alkanes
Low reactivity
1- Combustion:
• Alkanes react with oxygen.
• CO2, H2O, and energy are produced.
• Alkane + O2 CO2 + H2O + heat
CH4 + 2O2 CO2 + 2H2O + energy
Sources of Alkanes
• Natural gas
– 90 to 95 percent methane
– 5 to 10 percent ethane, and
– a mixture of other low-boiling alkanes, chiefly propane, butane, and 2-
methylpropane.
• Petroleum
– A thick liquid mixture of thousands of compounds, most of them
hydrocarbons formed from the decomposition of marine plants and
animals.
OM2029 12
26/09/2016
Alkenes and Alkynes
Alkenes and Alkynes
Saturated compounds (alkanes):
Have the maximum number of hydrogen
atoms attached to each carbon atom.
Unsaturated compounds:
Have fewer hydrogen atoms attached to
the carbon chain than alkanes.
• Containing double bond are alkenes.
CnH2n
• Containing triple bonds are alkynes.
CnH2n-2
OM2029 13
26/09/2016
Naming Alkenes & Alkynes
Using the IUPAC alkane names:
Alkene names change the end to -ene.
Alkyne names change the end to -yne
Naming Alkenes & Alkynes
CH2= CH ─ CH2─ CH3 1-butene
1 2 3 4
CH3─ CH=CH─ CH3 2-butene
1 2 3 4
CH3
|
CH3─ CH=C─CH3 2-methyl-2-butene
4 3 2 1
CH3─ CC ─ CH3 2-butyne
1 2 3 4
OM2029 14
26/09/2016
Naming Alkenes & Alkynes
CH3─ CH2─ CC ─ CH3 2-pentyne
5 4 3 2 1
CH3
CH3─ CH2─ C=CH ─ CH3 3-methyl-2-pentene
5 4 3 2 1
CH2 – CH3
CH3─ CH2─ C=CH ─ CH3 3-ethyl-2-pentene
5 4 3 2 1
Polymerisation
More reactive than Alkanes
Hydrogenation:
• A hydrogen atom adds to each carbon atom of a double
bond.
• A catalyst such as platinum is used.
H H H H
│ │ Pt │ │
Pt
H–C=C–H + H2 H– C – C– H
│ │
H H
ethene ethane
OM2029 15
26/09/2016
Test your knowledge..
Give the IUPAC name.
1.
2.
Exercise:
1. Write the molecular formula and give the structural
formula of a) Heptane b) Decene c) Butyne
2. Which family of hydrocarbon does C4H10 belong to?
How many C – C bonds are present? Are these
unsaturated or not?
3. Study the following structural formula
and answer the question carefully.
a) Which one of these is an saturated hydrocarbon?
b) Write the molecular formula of both compounds
and identify the family of hydrocarbons to which they
belong.
4. An Alkene has 2 carbon atoms. Write down the
molecular formula, structural formula and name of this
compound.
OM2029 16
