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Molecular formula: The formula which shows the actual number of each type of atom
Empirical formula: shows the simplest whole number ratio of atoms of each element in the compound
General formula: algebraic formula for a homologous series e.g. CnH2n
Structural formula shows the minimal detail that shows the arrangement of atoms in a
molecule, eg for butane: CH3CH2CH2CH3 or CH3(CH2)2CH3,
Displayed formula: show all the covalent bonds present in a molecule
H
H C H
H
H
Skeletal formula shows the simplified organic formula, shown by removing hydrogen atoms from alkyl chains,
leaving just a carbon skeleton and associated functional Groups.
OH
2-methylbutane
But-2-ene
Butan-1-ol
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cyclohexane
cyclohexene
Homologous series are families of organic compounds with the same functional
group and same general formula.
They show a gradual change in physical properties (e.g. boiling point).
Each member differs by CH2 from the last.
same chemical properties.
Functional group is an atom or group of atoms which when present in different molecules
causes them to have similar chemical properties
homologous
series
functional
group
prefix / suffix
(* = usual use)
example
Alkane
C
CH3CH2CH2CH3
-ane
Alkenes
H
C
suffix -ene
C
C
H
Haloalkanes
OH
OH
1-chloropropane
H
suffix -al
H
Propan-1-ol
prefix chlorobromoiodo-
halogen
Aldehydes
suffix* -ol
prefix
hydroxy-
propene
Alcohols
Butane
prefix formyl-
Cl
Cl
ethanal
H
O
suffix* -one
prefix oxo-
Ketones
carboxylic
acids
O Ethanoic acid
OH
H
OH
H
O
C
Propanone
OH
-yl oate
methylethanoate
Esters
H
H
O
C
H
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CH2
3,5-dimethylheptane
H3C
CH
CH2
CH
CH3
CH2 6
CH3 7
code
no of
carbons
meth
eth
prop
but
pent
hex
hept
oct
non
dec
10
C3 C
C1
Butan-1-ol
H
C
methylpropane
CHCl3
trichloromethane
H C H
H
Br
Br
CH2FCCl2CH2CH3
CH2FCH2CHBrCH2CH3
CH2OHCHBrCH=CH2
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2,3-dibromopentane.
2,2-dichloro-1-fluorobutane.
3-bromo-1-fluoropentane
2-bromobut-3-en-1-ol
Halogenoalkanes
Class the halogen as a substituent on the C chain and use the
suffix -fluoro, -chloro, -bromo, or iodo. (Give the position
number if necessary)
Alcohols
These have the ending -ol and if necessary the position
number for the OH group is added between the name stem
and the ol
Br H
2-bromobutane
OH
Butan-2-ol
CH3
CH
CH2
CH3
4
O
2-hydroxypropanoic acid
H3C CH C
OH
OH
Ethane-1,2-diol
HO CH2 CH2 OH
If there are two or more -OH groups then di, tri are used.
Add the e on to the stem name though
Aldehydes
An aldehydes name ends in al
It always has the C=O bond on the
first carbon of the chain so it does
not need an extra number. It is by
default number one on the chain
H2C
OH
HC
OH
H2C
OH
propane-1,2,3-triol
Ketones
Ketones end in -one
Ethanal
If two ketone groups then
di is put before one and
an an e is added to the
stem
Carboxylic acids
These have the ending oic acid but no number is
necessary for the acid
group as it must always be
at the end of the chain.
The numbering always
starts from the carboxylic
acid end
Propanone
H
Pentane-2,4-dione
O
C
Ethanedioic acid
HO
OH
Ethanoic acid
Esters
Esters have two parts to their names
The bit ending in yl comes from the alcohol that has
formed it and is next to the single bonded oxygen.
The bit ending in anoate comes from the carboxylic acid.
(This is the chain including the C=O bond)
H
O
C
H
methylpropanoate
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Isomers
Structural isomers: same molecular formula different structures (or structural formulae)
Structural isomerism can arise from
OCR does not split structural isomers
into the different categories. They are
all classed as structural isomers.
Chain isomerism
Position isomerism
Functional group isomerism
Chain isomers: Compounds with the same molecular formula but different
structures of the carbon skeleton
H
H
H
C H
H C H
H
H
pentane
2-methylbutane
2,2-dimethylpropane
Position isomers: Compounds with the same molecular formula but different structures
due to different positions of the same functional group on the same carbon skeleton
Br
1-bromopropane H
Br
2-bromopropane
Functional group isomers: Compounds with the same molecular formula but
with atoms arranged to give different functional groups
H
H
H
O
ethanol: an alcohol
C
H
Methoxymethane: an ether
H
C
CH3CH2CH2CH2CH=CH2
hexene- alkene
C
H
H
H
Note: alkene and cyclo alkanes have the same general formula. Hexene
and cyclohexane have the same molecular formula but have a different
functional group
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Stereoisomerism
Stereoisomers have the same structural formulae
but have a different spatial arrangement of atoms
H
H
H
C
C
H
H
C
H
C
H
C
H
C
C
H
C
H
H
Cl
C
H
H
But-1-ene
Cl
H
C
Z-1,2-dichloroethene
But-1-ene is a structural isomer of But-2ene but does not show E-Z isomerism
Priority
group
side 2
Cl
C
E -but-2-ene
Priority
group
side 1
Z- but-2-ene
H
C
Cl
E-1,2-dichloroethene
H
C
H
C
C
H
C
H
H
Z- but-2-ene
E- but-2-ene
Cis- but-2-ene
trans- but-2-ene
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Introduction to Mechanisms
To understand how the reaction proceeds we must first understand how bonds are broken in organic mechanisms
There are two ways to break a covalent bond:
1.HOMOLYTIC FISSION:
DEFINITION
OR
X: -
Y+
X+
Y:
+
xx
Cl
xx
xx
Cl
xx
Cl
xx
Cl
xx
HO:-
OH
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+ X-
Percentage Yield
actual yield
percentage yield =
theoretical yield
x 100
Example : 25g of Fe2O3 was reacted and it produced 10g of Fe. What is the
percentage yield?
Fe2O3 + 3CO
2Fe + 3 CO2
% yield =
percentage atom
economy
x 100
sum of molecular masses of all products
Example: What is the % atom economy for the following reaction where Fe is the
desired product assuming the reaction goes to completion?
Fe2O3 + 3CO
2Fe + 3 CO2
% atom economy =
(2 x 55.8)
x 100
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2.1.2 Alkanes
Hydrocarbons from crude oil
Hydrocarbon is a compound consisting of hydrogen and carbon only
20 C
petrol/gasoline
Fractional Distillation:
40 C
naptha (chemicals)
110 C
Crude
oil
180 C
diesel oil
250 C
300 C
Furnace
fuel oil
lubricating oils
340 C
Oil is pre-heated
then passed into column.
The fractions condense at different heights
The temperature of column decreases upwards
The separation depends on boiling point.
Boiling point depends on size of molecules.
The larger the molecule the larger the van der waals forces
Similar molecules (size, bp, mass) condense together
Small molecules condense at the top at lower temperatures
and big molecules condense at the bottom at higher temperatures.
bitumen
This is a physical process
involving the splitting of
weak van der waals forces
between molecules
H
H
C
H
H
H
The increasing boiling points of the alkane homologous series can be explained by the increasing
number of electrons in the bigger molecules causing an increase in the size of the van der Waals
between molecules.
The shape of the molecule can also have an effect on the size of the van der Waals forces. Long chain
alkanes have a larger surface area of contact between molecules for van der waals to form than compared to
spherical shaped branched alkanes and so have stronger van der waals and higher boiling points.
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Hydrocarbons as fuels
Fuel : releases heat energy when burnt
Complete Combustion
In excess oxygen alkanes will burn with complete combustion
Cracking
Cracking: conversion of large hydrocarbons to smaller molecules by breakage of C-C bonds
High Mr alkanes
Catalytic Cracking
Conditions:
Low pressure
High Temperature (450C)
Zeolite Catalyst
Branched and cyclic hydrocarbons burn more cleanly and are used to give
fuels a higher octane number
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Synthesis of chloroalkanes
CH3Cl + HCl
methane
chloromethane
To understand this reaction fully we must look in detail at how it proceeds step by step.
This is called its mechanism
2Cl.
Cl2
HCl + .CH3
CH3Cl + Cl.
DEFINITION
A Free Radical is a reactive species which
possess an unpaired electron
All propagation steps have a free radical in the reactants and in the products.
As the Cl free radical is regenerated, it can react with several more
alkane molecules in a CHAIN REACTION
.CH + .CH
3
3
Collision of two free radicals does not generate further free radicals:
the chain is TERMINATED.
CH3CH3
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2Br
CH3CH2CH3 + Br
HBr + CH3CH2CH2
.
CH3CH2CH2 + Br2
.
CH3CH2CH2Br + Br
CH3CH2CH2 + Br
CH3CH2CH2Br
CH3CH2CH2 + CH3CH2CH2
CH3CH2CH2CH2CH2CH3
Further substitution
Excess Cl2 present will promote further substitution and could produce CH2Cl2, CHCl3 and CCl4
These reactions could occur
CH3Cl + Cl2
CH2Cl2 + Cl2
CHCl3 + Cl2
CH2Cl2 + HCl
CHCl3 + HCl
CCl4 + HCl
CH3Cl + Cl.
HCl + .CH2Cl
. CH Cl + Cl
CH2Cl2 + Cl .
2
2
You should be able to write overall reaction equations for various reactions
Example 1. Write the overall reaction equation for the formation of CCl4 from CH4 + Cl2
CH4 + 4 Cl2
CCl4 + 4 HCl
Example 2. Write the overall reaction equation for the formation of CFCl3 from CH3F + Cl2
CH3F + 3 Cl2
CFCl3 + 3 HCl
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2.1.3 Alkenes
H
C
H
C
Ethene
Numbers need to be
added to the name when
positional isomers can
occur
H
C
H
Propene
But-1-ene
But-2-ene
C-C pi bond
Formation of bond
p orbitals
The bond is formed by
sideways overlap of two p
orbitals on each carbon atom
forming a -bond above and
below the plane of molecule.
C-C sigma bond
C-C pi bond
H
C
H
H
C
CH3
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alkane
H
C
+ H2
C
H
ethene
ethane
+ Br2
Br
Br
1,2-dibromoethane
H
H
C
H
C
+ H
Br
Br
Br
Br
The INTERMEDIATE
formed, which has a
positive charge on a
carbon atom is called a
CARBOCATION
:Br -
Br-
H3C
H
H
H + HBr
Br
But-2-ene
+
H
Br
H
CH3
H3C
2-bromobutane
C
H
:Br
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CH3
H3C
Br
CH3
14
If the alkene is unsymmetrical, addition of hydrogen bromide can lead to two isomeric products.
But-1-ene will form a mixture of 1-bromobutane and 2-bromobutane on reaction with hydrogen
bromide
:Br H
+
C
+
H2C
CH2
H3C
Br
CH
CH2 CH3
CH3
Br
Major
product
90%
:Br H
H
+
CH2
CH2 CH3
Br
CH3CH2OH (l)
Reagent : steam
Essential Conditions
Addition Polymers
Poly(alkenes) like alkanes are unreactive due to
the strong C-C and C-H bonds
Polymer
polyethene
Ethene
H
H
C
CH3
propene
CH3
CH3 H
CH3 H
CH3 H
poly(propene)
Poly(propene) is recycled
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CH3
H3C CH CH
H
C
H3C
CH3
CH3
CH3
C
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