Hydrocarbons

PRESENTER: SHANNON SMITH

 2.5 Explain the steps
2.1 Identify 2.3 Explain the steps
2.2 Describe selected 2.4 Describe selected involved in the 2.6 Describe selected 2.7 Describe selected
homologous series of involved in the
chemical reactions of chemical reactions of mechanism of selected chemical reactions of reactions of
organic/carbon mechanism of free
alkanes. alkenes. chemical reactions of alcohols. halogenoalkanes.
compounds. radical substitution.
alkene function group

2.10 Explain the steps

2.8 Explain the steps 2.13 Perform suitable 2.14 Describe the
involved in 2.11 Describe selected
involved in the 2.9 Describe selected 2.12 Describe selected laboratory tests for chemical reactions of
mechanisms of chemical reactions of
mechanism of selected chemical reactions of chemical reactions of functional groups in primary amines
selected chemical carboxylic acids (R-
reactions of carbonyl compounds. esters. carbon compounds (RNH2) with dilute
reactions of carbonyl COOH).
halogenoalkanes. referred to above; acid.
compounds.

2.15 Describe selected 2.16 Explain the steps

chemical reactions of involved in the 2.17 Describe selected 2.18 Describe the
2.19 State uses of azo
benzene mechanism of selected chemical reactions of formation of an azo
compounds.
methylbenzene and chemical reactions of phenol. compound.
nitrobenzene. benzene.

Objectives
 The Alkanes

Alkanes (general formula CnH2n+2), are

unreactive towards most chemical reagents.

 Very small electronegativity difference.

 C-C bonds are non polar (this reduces their
vulnerability to chemical attack).
 So are not attacked by reagents such as
acids and alkalis.
Combustion of
alkanes
 Alkanes undergo combustion in
excess oxygen or air to form carbon
dioxide and water.
CH4(g) + 2O2(g) → CO2(g) + 2H2O(g)

 Incomplete combustion produces

carbon monoxide (and/or carbon).
CH4(g) + O2(g) → CO(g)+ 2H2O(g)
Cracking is the thermal decomposition of Cracking of alkanes
alkanes into shorter-chain alkanes and alkenes

With a catalyst
 Carried out at 400° - 500°C.
 Using catalyst of SiO2 and Al2O3.
C13H28(g) → C8H18(g) + C3H6(g) + C2H4(g)
Without a catalyst
 Carried out at 700° - 900°C.
Thermal Cracking is important to produce
 Shorter-chain alkanes needed for petrol.
 Shorter-chain alkanes needed for making
many chemicals, e.g. plastics
 Also a source of hydrogen.
CH3CH3(g)→ CH2=CH2(g) + H2(g)
 Halogenation of
alkanes
 No reaction in the dark.
 Substitution reaction in uv light.
 In chlorination of alkanes, one or
more hydrogen atoms are replaced
by chlorine atoms.
 With excess chlorine more and more
hydrogen atoms are replaced.

Substitution reaction is a reaction in which

one atom or group of atoms is replaced by
another.
Reaching mechanisms show the steps in bond Mechanism and
breaking and bond making when reactants are
converted to intermediates and then to electron movement
products.

Homolytic fission: The two shared electrons

in the bond are split equally between the two
atoms.

Free radicals: Are atoms or groups of atoms

with unpaired electrons.

Heterolytic fission: The two shared electrons

in the bond are split unequally between the
two atoms. One of atoms keeps both pairs of
electrons and so becomes negatively charged.
The other becomes electron deficient so is
positively charged.
Free radical substitution
hv
in alkanes
Initiation
 UV light causes the Cl-Cl bond to
break by homolytic fission.
Propagation
 Free radicals are so reactive that they
can attack the relatively unreactive
methane, forming a methyl free
radical.
 The methyl free radical can then
attack another chlorine molecule
forming chlorine free radicals.
 If there is excess chlorine this
process can continue until all the
hydrogen atoms in methane have
been replaced.
Free radical
substitution in alkanes
Termination
 Two free radicals combine to form a
single molecule.
 This stops the chain reaction in the
propagation step.
 The reaction finishes when there are no
more free radicals left to react.
 Alkenes

Alkenes (general formula CnH2n), are

unreactive towards most chemical reagents.

 Although non-polar, more reactive than

alkanes.
 C=C double bond is an electron-rich area..
 So are attacked by positively charged
reagents.
 Electrophilic addition

An electrophile is a positively charged (or

partially positively charged) reagent which
attacks an electron-rich area of a molecule.

Addition reactions are reactions in which a

single product is formed from two reactant
molecules and no other product is made.
Addition reactions with
hydrogen halides
 When ethene is passed through
hydrogen bromide dissolved in an inert
solvent, bromoethane is formed.
 The mechanism is electrophilic
addition.
 HBr is a polar molecule, acts as an
electrophile.
 An electron pair from the double bond
in ethene forms a bond with the H atom
to form a positively charged
carbocation.
 Br atom gains control of the electron
pair and the H-Br bond breaks
heterolytically.
 The Br- ion attacks the + carbocation
forming bromoethane.
 Reaction of HBr with
 When the double bond is not quite in other alkenes
the middle, a mixture of products is
formed.
 HBr with propene gives 2
possibilities.
 The partially positive H atom attacks
the electron rich double bond.
 An electron pair from the double
bond forms a bond with the H atom
to form a + carbocation., leaving a –
Br ion.
 The more electronegative atom, the
halogen, adds to the C atom with is
connected to the least number of H
atoms.
Reactions of alkenes
with bromine
 Alkenes react with bromine liquid to
form dibromoalkanes.
CH2=CH2 + Br2 → CH2Br-CH2Br
 The mechanism is similar to that for
hydrogen halides.
 Br2 acts as an electrophile.
 As the Br2 and ethene molecules
approach each other, the high
electron density in the C=C bond
repels the electron pair in the Br2
single bond.
 This causes Br2 to be polarised.
 Reaction of alkenes
 The Brδ+ end attacks the area of high with bromine
electron density in the double bond.
 An electron pair from the double
bond in ethene forms a bond with the
Brδ+ and a positively charged
carbocation is formed.
 At the same time the other Br atom
gains control of the electron pair in
the Br2 to form a Br- ion i.e. the Br-
Br bond breaks heterolytically.
 The Br- ion then attacks the +
carbocation and the addition product,
1,2-dibromoethane is formed.
 Chlorine acts in a similar way
The bromine water
test for alkenes
 Liquid bromine is very hazardous, so
we use aqueous bromine (bromine
water) to test for the C=C bond.
 On addition of bromine water to
unsaturated compounds, the colour
changes from orange/red-brown to
colourless.
 The reaction is an addition reaction
similar to that occurring with liquid
bromine but a mixture of colourless
addition of products is obtained.
An unsaturated compound contains C=C
double bonds.
 Reaction of alkenes
 The is another example of an with concentrated

addition reaction.
Ethene reacts at room temperature to
sulphuric acid
form ethyl hydrogen sulphate,
CH3CH2OSO3H.
 The electrophile is the partially
charged H atom in H2SO4.
 When water is added to the product
and the mixture warmed, ethanol is
formed.
 The sulphuric acid is also reformed.
 The overall reaction can be thought
of as the addition of the H and OH
from the water across the double
bond.
Esters
 The –COO- group is often called an
ester link

Esters are compounds that contain the –COO-

group.
Naming Esters
 The name begins with the alkyl (or
aryl) group from the alcohol.
 The name ends with the part coming
from the carboxylic acid.
Hydrolysis Esters
 Breakdown with water..
 Heating the ester under reflux with
an acid or alkali speeds up
hydrolysis. Reaction is slow
otherwise.
 Acid or alkali acts as a catalyst.
 Reflux to prevent loss of the volatile
vapours of the ester and alcohol.
 The vapours rise and then condense
on the colder parts of the condenser.
Then drip back into the flask.
Acid Hydrolysis
 Reverse of the preparation of an ester
from an alcohol and a carboxylic
acid.
 Ester is heated with diluted sulphuric
acid.
 The reaction is reversible
 The ester may not be fully
hydrolysed.
 An carboxylic acid and an alcohol
are formed.
 For an ester RCOOR’ the carboxylic
acid arises from the RCO part of the
alcohol from the –OR part.
Alkaline Hydrolysis
 The ester is heated with NaOH(aq)
or other suitable base.
 The reaction is not reversible
 The ester is fully hydrolysed.
 An alcohol and the salt of a
carboxylic acid are formed.
 For an ester RCOOR’, the salt of the
carboxylic acid arises from the RCO-
part of the ester and the alcohol from
the –OR part.
 Deducing the empirical formula
Calculate the empirical formula of a compound of carbon, hydrogen and iodine that contains 8.45% carbon,
2.11% hydrogen and 89.44% iodine by mass. (Ar values: C = 12.0, H = 1.0, I = 127.0).

Step 1: Assume that we have 100g of the compound, then each of the percentages can be converted to mass,
that is 8.45 g of carbon, 2.11 g hydrogen and 89.44 g of iodine.
Divide mass by Ar to determine number of moles of each atom in the compound.

Step 2: Divide by lowest number to get mole ratio:

Step 3: Write the formula showing the simplest ratio: CH3I.

Deducing the
molecular formula
We can determine the molecular
formular if we know:
 The empirical formula.
 The molar mass of the compound.
The molar mass of a compound can be
found by:
 Weighing a known volume of gas.
 Using a mass spectrometer
 Deducing the molecular formula
Determine the molecular formula of 6.00 g of a hydrocarbon contains 4.80 g of carbon and 1.20 g of
hydrogen. The relative molecular mass of the hydrocarbon is 30.

Step 1: Divide mass by Ar to determine number of moles of each atom in the compound.

Step 2: Divide by lowest number to get mole ration:

Step 3: Write the formula showing the simplest ratio: CH3.

 Deducing the molecular formula
Determine the molecular formula of 6.00 g of a hydrocarbon contains 4.80 g of carbon and 1.20 g of
hydrogen. The relative molecular mass of the hydrocarbon is 30.

Step 4: Find the empirical formula mass: 12.0 + ( 3 x 1.0) = 15.0

Step 5: Divide the molar mass of the compound by the empirical formula mass.

Step 6: Multiply each atom in the empirical formula by the number deduced in Step 5: CH 3 x 2 = C2H6.
 Molecular formula using Avogadro’s Law
Propane contains carbon and hydrogen only. When 25cm3 of propane reacts with exactly 125cm3 oxygen,
75cm3 of carbon dioxide is formed. Deduce the molecular formula of propane and write a balanced equation
for the reaction.
Naming simple
organic compounds
IUPAC rules:
 The stem tells us how many carbon
atoms there are on the main chain.
 A suffix is added to the end of the
stem and tells us about the functional
groups present.
 A prefix for some homologous series
appears before the stem.
Naming Simple
Organic Compounds
Naming branched-
chain alkanes
IUPAC rules:
 The position of side chains/functional
groups is shown by numbering the
carbons.
 The longest possible chain of carbons
atoms is chosen.
 Numbering starts at the end that gives
the smallest number possible for the
side chain.
 The side chain prefixes the stem name.
 The side chain is named according to
the number of carbon atoms it
contains.
 More than one side
chain?

 If there is more than one of the same alkyl

side chain/functional group, use the
prefixes di-for two groups, tri-for three,
tetra-for four.
Functional group
position
The numbering of functional groups
along the side chain follows many of the
general rules. But note that the number
given to the C=C bond in alkenes is
between the prefix and the stem.
 Chain Isomerism

Isomers are molecules that have the same

molecular formula but the atoms are arranged
differently.

Structural isomerism are compounds with

the same molecular formular but different
structural formulae.

Chain isomerism is where the isomers differ

in the arrangement of carbon atoms in their
carbon skeleton.
 Functional group
Functional group isomerism is where the isomerism
molecular formula of the isomers is the same
but the functional groups are different.
 Positional Isomerism

Positional isomerism is where the position of

the functional group is different in each
isomer.
Isomerism and bond
rotation
 Stereoisomerism

Stereoisomerism is where two (or more)

compounds have the same atoms bonded to
each other but the atoms have a different
arrangement in space.

There are 2 types:

 Geometrical isomerism (cis-trans
isomerism)
 Optical isomers.
Geometrical isomerism occurs when the
substituent groups on either side of a double
bond are arranged either on the same side (cis)
or on the opposite sides (trans).
 Optical isomerism
Optical isomerism happens when four
different groups are attached to the central
carbon atom. The two isomers formed are
mirror images of each other. They are not
identical because they cannot be
superimposed.

 With chain hydrocarbons, we can condense

the formula even more.
 Side branches are shown in brackets.
 Optical isomerism
 In ethane and ethene the electrons are
localised.
 Benzene can be represented as a composite
structure called a resonance hybrid.
 Carbon toms have 3 sp2 orbitals (one to
each hydrogen atom and 2 other carbon
atoms).
 The single p orbital left over each carbon
atom overlap sideways to form a
delocalised system of ℼ bonds.
 These compounds are called aryl
compounds.

Delocalised means the electrons move freely

over molecular orbitals extended over 3 or
more atoms..
Resonance