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2021-2022 - Properties of Hydrocarbons
2021-2022 - Properties of Hydrocarbons
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PHYSICAL PROPERTIES OF
HYDROCARBONS
The table below lists the melting and boiling point of some
straight chain alkanes
Alkanes (also known as paraffins) are saturated hydrocarbons
The general formula of alkanes is CnH2n+2
All the bond angles in molecule are ≈109.5◦
Compound Structure Atom Mr State Bp (˚C) Mp(˚C)
C
2,2-dimethylprop 283
ane
alkanes Density
Methane 0.424
Ethane 0.446
Less Compact packing
Propane 0.502
Butane 0.600
Pentane 0.626
Hexane 0.658
Compact packing
heptane 0.684
Density
• For example:
Molecule Density
2,2-dimethylpropane 0.591
2-methylbutane 0.620
Pentane 0.626
Solubility
• All alkanes are non-polar. This is due to the very small
difference between the electronegativity of carbon and
hydrocarbon
• Alkanes are insoluble in water (polar solvent) as they cant
form hydrogen bonds with water molecules
• Alkanes are soluble in non-polar solvents such as benzene
and tetrachloromethane
Evi Elfrida | SLHS | Organic chemistry
CRACKING oil fraction
HYDROCARBONS to produce more
useful products
B. The three main types of reagents usually encountered in organic reactions are :
1. Free Radicals
2. Electrophiles
3. Nucleophiles
2. Heterolytic Fission
• Breaking of a covalent bond such as that both e- go to same atom
• Form positive and negative ions
c. The relative stability of a free radical depends on the electron density of the radical.
The higher the electron density, the less reactive it is (because the degree of 'electron
deficiency' is reduced) and the more stable it is.
d. The stability of the free radicals decreases in the order :
30 > 20 > 10 > methyl free radical
e. The reactivity of the free radicals increases in the order :
methyl free radical >10 > 20> 30
f. Carbonium ions (or carbocations) are electrophiles where the positive charge is localized on a carbon
atom
g. The more alkyl groups (electron releasing) that are attached to the positive charge carrying carbon atom,
the more stable is the carbonium ion
e. Examples are OH- , RCOO-, Cl- , Br-, I-, F-, H2O and carbanions.
f. Carbanions are nucleophiles where the negative charge is localized on a carbon atom
Examples are :
(a) Reaction between alkene and halogen
2. Addition Reaction
(b) Reaction between alkene and HCl
Uv light
HYDROGENATION
1. Addition of hydrogen (Hydrogenation) or Catalytic Hydrogenation
• the reaction is carried out under pressure in the presence of a metallic catalyst
such as platinum, nickel or palladium.
HYDROGENATION
1. Addition of hydrogen (Hydrogenation) or Catalytic Hydrogenation
•Example :
1. Propene + H2 🡪 propane
2. 2-methyl-2-hexene + H2 🡪.................
3. 1,3-butadiene + H2 🡪 ..........................
4. 4-methylcyclohexene + H2 🡪............... Evi Elfrida | SLHS | Organic chemistry
Manufacture of Margarine
Addition of hydrogen (Hydrogenation) or Catalytic Hydrogenation
HALOGENATION
2. Addition of X2 (Halogenation)
Examples
Reaction 1
Reaction 2
HALOGENATION
3. Addition of HX (Hydrohalogenation)
3. Addition of HX (Hydrohalogenation)
2. An unsymmetrical alkene
• The reaction between HBr is highly regioselective. It was noted by a Russian chemist,
Vladimir V. Markovnikove, who purposed the Markovnikove’s rule in 1869
• When a hydrogen halide adds to an Unsymetrical alkene, two possible products will be
formed
Anti Markovnikov
Propagation Steps
Termination Steps
There are also Termination Steps, but we do not concern about the termination steps as they are just the radicals
combining to create waste products.
Evi Elfrida | SLHS | Organic chemistry
reactions of alkenes
Anti Markovnikov
Peroxides
HYDRATION
• Hydration should not be confused with hydrogenation
• Hydration mean adding water, but we should consider it as adding H and OH
to the two atoms in a C=C double bond
• This reaction is usually done by heating the alkene with steam and passing
the mixture over a catalyst of phosphoric acid
• The hydration of ethene forms ethanol
• Under normal conditions, alkenes dont react with water. However, they react
with steam under high temperature and pressure and in the present catalyst to
form alcohol
• The catalyst used is ussually concentrated phosphoric acid (H3PO4) adsorbed
on the surface of an inert solid such as silica
OXIDATION TO DIOLS
• A diol is a compound containing two OH (alcohol) groups
• The oxidising agent is potassium manganate(VII) in acid conditions
(usually dilute sulfuric acid).
a. Potassium manganate(VII) provides and oxygen atom (oxidation)
b. The water in the solution provides another oxygen atom and two
hydrogen atoms, so there is the addition of two OH groups across the
double bond KMnO4
+ MnO2
Cold
• The colour of the potassium manganate(VII) solution changes from purple to brown (MnO 2)
• This colour change means that this reaction can be used to distinguish alkenes from alkanes
• Alkanes don’t have double bond and so are not oxidised in this way
reactions of alkenes
(Ethane-1,2-diol)
• A diol is an organic compound that has two –OH GROUPS in its molecule
• If the unsaturated C atom is bonded to 2 alkyl group, the double bond will break and the groups are
oxidised to produce a ketone