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ORGANIC CHEMISTRY

What is an Organic Compound?


An Organic compound contains carbon and hydrogen atoms covalently bonded.

Three Homologous Series


(This is what you need to know for unit 1)

ALKANES
(CnH2n+2): hydrocarbons, mainly used as fuel

ALKENES
(CnH2n): hydrocarbons with double bonds, used to make polymers

HALOALKANES
(CnH2n+1X): contain halogen atoms, CFCs, which are being phased out

What is a Homologous Series?


Members of a homologous series all have: the same general formula similar chemical properties physical properties show a trend the same functional group

Naming Alkanes
Alkanes are named after the longest chain of carbon atoms in the molecule
No of Carbon Atoms Formula
CH4

Name
Methane

1 2 3 4 5 6

C2H6
C3H8 C4H10 C5H12 C6H14

Ethane
Propane Butane Pentane Hexane

Remember - Monsters Eat Pretty Blondes!!!

Representing Formulae
Molecular formula Actual numbers of atoms of each element present in a molecule e.g. C4H10
Empirical formula Simplest ratio of atoms of each element present in a molecule e.g. C2H5

Representing Formulae
Structural formula
Shows the structure of the molecule
H H H H | | | | HCCCCH | | | | H H H H

The structural formula can be abbreviated to emphasise the carbon skeleton


CH3CH2CH2CH3

Representing Formulae
Displayed

formula (shows every bond in the molecule)

Naming Alkanes
Branches are named after the number of carbon atoms that they contain: 1 carbon = methyl 2 carbons = ethyl (very very rare for unit 1)

Naming Alkanes
The position of the branch is indicated by a number The lowest possible number is used
H | HCH | H || H H | | | HCCCCH | | | | H H H H

2 - methylbutane

Naming Alkanes
H | HCH | H | H | | | HCCCH | | | | H H | HCH | H

2,2-dimethylpropane

Naming Alkanes
2 of a functional group di 3 of a functional group tri 4 of a functional group tetra

Cyclo alkanes
Rings of carbon atoms are known as cycloalkanes CnH2n Note a cyclo alkane has the same molecular formula as the corresponding straight chain alkene. They are Functional group isomers a type of structural isomer E.g.butene and cyclobutane are both C4H8

Naming haloalkanes

R-F: fluoroalkane R-Cl: chloroalkane R-Br: bromoalkane R-I: iodoalkane

Naming HaloAlkanes
The position of the halogen must be stated
Example 1-chloro propane
Cl H H | | | HCCCH | | | H H H

2-chloro propane
H Cl H | | | HCCCH | | | H H H

Naming HaloAlkanes
If there are more than 1 halogen:they must be listed in alphabetic order Example

2-bromo-1-chloropropane Cl Br H | | | HCCCH | | | H H H

2-chloro-1,1,1, trifluoropropane H Cl F | | | HCCCF | | | H H F

Naming Alkenes
The position of the double bond is indicated by the number of the starting position
Example

But-1-ene

H H | | HC CCCH | | | | H H H H

Rules for naming organic molecules


1. Count the longest chain. That gives the name of the chain 2. Look for branches and functional groups off the main chain 3. If 2 of the same di, 3 of the same tri, 4 of the same tetra 4. Put a position number for each, remember start from the shortest end (lowest number.) 5. Where more than one group they must be in alphabetic order

STRUCTURAL ISOMERS
These are compounds with the same molecular formula, but with different structural formulae H | e.g. Isomers of C4H10 HCH
H H H H | | | | HCCCCH | | | | H H H H

| H | H | | | HCCCH | | | H H H

There are three types of structural isomerism

Chain Isomerism Position Isomerism Functional Group Isomerism Remember - These are all forms of structural isomerism - molecules have the same molecular formulae, but different structures

CHAIN ISOMERISM:
the

carbon chains are arranged differently. Example Butane and Methyl Propane Both Isomers of C4H10
H | HCH | H | H | | | HCCCH | | | H H H

H H H H | | | | HCCCCH | | | | H H H H

POSITION ISOMERISM
the

functional group is at a different position on the chain. Example 1 chloro propane and 2 chloro propane
Cl H H | | | HCCCH | | | H H H H Cl H | | | HCCCH | | | H H H

FUNCTIONAL GROUP ISOMERISM


the

isomers belong to different homologous series. Example Butene and Cyclobutane


H H | | HC CCCH | | | | H H H H
H H | | HCC H | | HCCH | | H H

THE OIL INDUSTRY

Fractional Distillation
Crude oil consists of a large number of different hydrocarbons. Most of these hydrocarbons are alkanes. The alkanes are separated according to their size by fractional distillation. Click here to see fractional distillation tower

Fractional Distillation
Crude oil is heated and vapour passed into the bottom of a tower Top of tower cooler than bottom I.e. temperature gradient This separates mixture into fractions depending on boiling points of hydrocarbons present Only those with low boiling points reach top Others condense in trays at different levels up the tower and are drawn off here

Questions
What is passed into the bottom of the tower Which hydrocarbons will be piped off at the bottom of the tower Why?

Cracking
Cracking converts large alkanes into smaller ones which are more useful for making plastics or motor fuel.

Types of Cracking
THERMAL CRACKING 700 1200 K , 70 atmos Makes alkenes for the plastics industry.

Types of Cracking
CATALYTIC CRACKING 720K; 1 atmos; zeolite catalyst consisting of Silicon dioxide and Aluminium oxide Products are mainly Branched and cyclic products, Products mainly for motor fuel

Example and Exercises


Cracking of Decane Decane Octane + Ethene C10H22 C8H18 + C2H4
Exercises 1. Write an equation for the thermal cracking of one molecule of C10H22 to give one molecule of propene and one molecule of an alkane only. 2. Write an equation to show the cracking of C14H30 to produce two molecules of butene plus one other molecule. 3. Write an equation to show the cracking of C14H30 to produce hexane and ethene 4. Write an equation to show the cracking of C14H30 to produce one molecule of propene and one molecule of propane and one other molecule 5. Write an equation to illustrate the thermal cracking of one molecule of tetradecane, C14H30in which the products are ethene and propene in the ratio of 2:1, and one other product

Combustion of Alkanes Complete


Combustion is reaction with oxygen. Complete combustion of a hydrocarbon produces water plus carbon dioxide. Example: ETHANE + OXYGEN CARBON DIOXIDE + WATER C2H6 + 3O2 2CO2 + 3H2O

Combustion of Alkanes Limited oxygen


When the supply of oxygen is limited, incomplete combustion occurs, and instead of CO2, carbon and carbon monoxide may be formed. Formation of carbon monoxide (CO: toxic) C2H6 + 2O2 2CO + 3H2O Formation of carbon (soot) C2H6 + 1O2 2C + 3H2O

POLLUTION PROBLEMS
Burning fossil fuels causes these pollutants:

Types of Pollution
CAUSE
S in fossil fuels reacts with air when burnt High temperature in car engine N2 and O2 in air react Lack of oxygen in car engine Heaters not serviced

POLLUTANT PROBLEM
SO2 Produces Acid Rain

NXOY: : NO, NO2, N2O CO C Unburned hydrocarbon

Causes acid rain and smog. Makes asthma, bronchitis worse CO - Toxic C - Unsightly Causes cancer, makes asthma, bronchitis worse

Exercise: write equations for the reactions below.


The formation of the following

a. b. c. d.

oxides of nitrogen from N2 and O2 in the car engine. NO N2O NO2 N2O4

Ways to reduce pollution


Fit catalytic converters in cars Use filters in power station chimneys to remove Sulphur dioxide ( CaO)

Many power stations burn fossil fuels. Sulphur impurities in fossil fuels react to form

Power Stations

SO2, which causes acid rain. Equation: S + O2 SO2 SO2 + H2O H2SO3 H2SO3 + O 2 H2SO4 Sulphur dioxide can be removed from emissions by reaction with calcium oxide. Equation: SO2 + CaO + O 2 CaSO4 The calcium sulphate is used as plaster. This is a neutralisation reaction The process is called flue gas desulfurisation

Catalytic Converters
Pollution from cars can be reduced by fitting a catalytic converter. This causes the pollutants to react amongst themselves. Less harmful substances are formed. Platinum or Rhodium Catalyst Watch this video clip

Summary of reactions in catalytic converter


In CO NOx Unburned Hydrocarbons Out CO2 N2 CO2 + H2O

Catalyst Converter Examples of reactions


2NO + 2CO N2 + 2CO2
2NO2 + 4CO N2 + 4CO2 N2O + CO N2 + CO2

C5H12 +16NO 8N2 + 5CO2 + 6H2O

Exercise
Write equations to show the reaction of these alkanes with NO: DECANE (C10H22) CYCLOHEPTANE (C7H14) BUTANE (C4H10) OCTANE (C8H18)

Global Warming and the Greenhouse effect


Visible radiation (sunlight) readily penetrates atmosphere and warms the earth Invisible infrared radiation is emitted by the earth and cools it down. Carbon dioxide traps infrared preventing it escaping earths atmosphere warms up (good in small amounts, bad if too much) Level of Carbon dioxide has been rising since industrial revolution, causing global warming Carbon dioxide is called a greenhouse gas Other greenhouse gases are water vapour and methane, the concentration of these in atmosphere tends to stay roughly the same

Carbon Neutral Activities


These are activities that produce no overall carbon dioxide emissions into the atmosphere