TOPIC:HYDROCARBON

ACADEMIC YEAR:2019-2020

NAME OF THE STUDENT:____________

ROLL NO:_________

TEACHER SIGN:
_______________
In organic chemistry, a hydrocarbon is an organic compound consisting
entirely of hydrogen and carbon
Aromatic hydrocarbons (arenes), alkanes, cycloalkanes and alkyne-based
compounds are different types of hydrocarbons.
Most hydrocarbons found on Earth naturally occur in crude oil, where
decomposed organic matter provides an abundance of carbon and
hydrogen which, when bonded, can catenate to form seemingly limitless
chains
General properties
Because of differences in molecular structure, the empirical formula remains
different between hydrocarbons; in linear or "straight-run" alkanes, alkenes and
alkynes, the amount of bonded hydrogen lessens in alkenes and alkynes due to
the "self-bonding" or catenation of carbon preventing entire saturation of the
hydrocarbon by the formation of double or triple bonds.

This inherent ability of hydrocarbons to bond to themselves is known

as catenation, and allows hydrocarbons to form more complex molecules, such
as cyclohexane, and in rarer cases, arenes such as benzene.
This ability comes from the fact that the bond character between carbon atoms
is entirely non-polar, in that the distribution of electrons between the two
elements is somewhat even due to the same electronegativity values of the
elements (~0.30), and does not result in the formation of an electrophile.
Generally, with catenation comes the loss of the total amount of bonded
hydrocarbons and an increase in the amount of energy required for bond cleavage
due to strain exerted upon the molecule; in molecules such as cyclohexane, this is
referred to as ring strain, and occurs due to the "destabilized" spatial electron
configuration of the atom.

In simple chemistry, as per valence bond theory, the carbon atom must follow the 4-
hydrogen rule, which states that the maximum number of atoms available to bond
with carbon is equal to the number of electrons that are attracted into the outer shell
of carbon. In terms of shells, carbon consists of an incomplete outer shell, which
comprises 4 electrons, and thus has 4 electrons available for covalent or dative
bonding.

Hydrocarbons are hydrophobic like lipids.

Some hydrocarbons also are abundant in the solar system. Lakes of liquid methane
and ethane have been found on Titan, Saturn’s largest moon, confirmed by
the Cassini-Huygens Mission. Hydrocarbons are also abundant in nebulae
forming polycyclic aromatic hydrocarbon (PAH) compounds.
 USAGE
Oil refineries are one way hydrocarbons are processed for
use. Crude oil is processed in several stages to form desired
hydrocarbons, used as fuel and in other products.

Tank wagon 33 80 7920 362-0 with hydrocarbon gas at Bahnhof

Enns (2018).
Hydrocarbons are a primary energy source for current
civilizations.

The predominant use of hydrocarbons is as a

combustible fuel source. In their solid form, hydrocarbons take
the form of asphalt (bitumen).

Mixtures of volatile hydrocarbons are now used in preference to the chlorofluorocarbons as

a propellant for aerosol sprays, due to chlorofluorocarbons' impact on the ozone layer.

Methane (CH4) and ethane (C2H6) are gaseous at ambient temperatures and cannot be readily liquefied by
pressure alone. Propane (C3H8) is however easily liquefied, and exists in 'propane bottles' mostly as a
liquid. Butane (C4H10) is so easily liquefied that it provides a safe, volatile fuel for small pocket lighters.
Pentane (C5H12) is a colorless liquid at room temperature, commonly used in chemistry and industry as a
powerful nearly odorless solvent of waxes and high molecular weight organic compounds,
including greases. Hexane (C6H14) is also a widely used non-polar, non-aromatic solvent, as well as a
significant fraction of common gasoline.

The C6 through C10 alkanes, alkenes and isomeric cycloalkanes are the top components
of gasoline, naphtha, jet fuel and specialized industrial solvent mixtures.

With the progressive addition of carbon units, the simple non-ring structured hydrocarbons have
higher viscosities, lubricating indices, boiling points, solidification temperatures, and deeper color.
At the opposite extreme from methane lie the heavy tars that remain as the lowest fraction in a
crude oil refining retort.

They are collected and widely utilized as roofing

compounds, pavement composition, wood
preservatives (the creosote series) and as extremely
high viscosity shear-resisting liquids.
Reactions
There are three main types of reactions:
Substitution reaction
Addition reaction
Combustion
Substitution reactions
Substitution reactions only occur in saturated hydrocarbons (single carbon–carbon bonds). In
this reaction, an alkane reacts with a chlorine molecule.
One of the chlorine atoms displaces a hydrogen atom. This forms hydrochloric acid as well as the
hydrocarbon with one chlorine atom.
CH4 + Cl2 → CH3Cl + HCl
CH3Cl + Cl2 → CH2Cl2 + HCl
all the way to CCl4 (carbon tetrachloride)

Addition reactions
Addition reactions involve alkenes and alkynes. In this reaction a halogen molecule breaks the
double or triple bond in the hydrocarbon and forms a bond.
 Combustion
Hydrocarbons are currently the main source of the world's electric energy and heat sources
(such as home heating) because of the energy produced when burnt.
Often this energy is used directly as heat such as in home heaters, which use
either petroleum or natural gas. The hydrocarbon is burnt and the heat is used to heat water,
which is then circulated.
A similar principle is used to create electrical energy in power plants.
Common properties of hydrocarbons are the facts that they produce steam, carbon dioxide and
heat during combustion and that oxygen is required for combustion to take place.

The simplest hydrocarbon, methane, burns as follows:

CH4 + 2 O2 → 2 H2O + CO2 + energy

In inadequate supply of air, carbon monoxide gas and water vapour are formed:
2 CH4 + 3 O2 → 2 CO + 4 H2O

Burning of hydrocarbons is an example of an exothermic chemical reaction. Hydrocarbons can

also be burned with elemental fluorine, resulting in carbon tetrafluoride and hydrogen
fluoride products.
 Classification of Hydrocarbons

Alkanes
Alkanes are saturated, open chain hydrocarbons
containing carbon-carbon single bonds. e.g., methane
(CH4), ethane (C4H6) propane (C3H8), etc.
These hydrocarbons are inert under normal conditions
[i.e., do not react with acids. bases and other
reagents). Hence, they were earlier known 88
paraffins.
Alkanes exhibit chain isomerism, position isomerism
.and conformational isomerism
Physical Properties of Alkanes

(i). The first four members are colourless gas, next thirteen members are colourless liquids and
next higher members are colorless solids.
(It can be explained on the basis of magnitude of attraction forces.)

(ii).Boiling point of alkanes decreases on branching.

BP ∝ VAF (van der Waals’ forces) ,VAF ∝ molecular mass or VAF ∝ SA (surface area)
So boiling point order can be given as n-octane > iso-octane> 2, 2, 3, 3-tetramethyl butane.

(iii).Alkanes with even number of carbon atoms have higher melting points as compared to next
higher or lower alkanes with odd number of carbon atoms.

(iv).Alkanes being non-polar in nature, soluble in non-polar solvents but insoluble in polar
solvent such as water.

Chemical Properties of Alkanes

(i) Halogenation of alkanes
(a) Chlorination
 (b) Iodination

Mechanism of halogenation of alkanes is free radical in nature, i.e., the attacking reagent is a halogen
free radical
(ii) Combustion

Due to the evolution of a large amount of heat during combustion, alkanes are used as fuels .

Alkenes
These are unsaturated non-cyclic hydrocarbons which have.sp2 -hybridization with 120°
bond angle.
Alkenes are also called olefins [oil. forming] which indicates their high reactive nature.
Alkenes have general formula Cn H2n, where n = 2,3,4 …
C2H4 (ethene), C3H6 (propene), etc.
Physical Properties of Alkenes
Alkenes as a class resemble alkanes in physical properties, except in types of isomerism and
difference in polar nature.

C1 to C3 are gases, the next fourteen are liquids and the higher members are solids.

Alkenes show a regular increase in boiling point with increase in size.

Chemical Properties of Alkenes

(i) Addition of halogens

(ii) Addition of hydrogen halides HCI, HBr, HI add up to alkenes to form alkyl halides as per their reactivity
order:HI > HBr > HCI
Addition reaction of HBr to unsymmetrical alkenes (Markownikoff’s rule) According to Markownikoffs rule,
the negative part of the addendum (adding molecule) gets attached to that carbon atom which possesses
lesser number of hydrogen atom.
Anti-Markownikoff addition or peroxide effect or kharash effect In the presence of organic peroxide,
addition of only HBr molecule on unsymmetrical alkene takes place contrary to the Markownikoffs rule.

Alkynes
These are unsaturated hydrocarbons with general formula CnH2n – 2 e.g., C2H2 (ethyne), C3H4 (propyne)
Alkynes also exhibit electrophilic addition reaction but less reactive than alkenes because the dissociation of
x-electron cloud requires more energy.
In alkynes, position of triple bond is determined by ozone (O3).H – C = C – H contains 3σ and 2π – bonds and
bond length is 120 pm. In acetylene. H – C – C bond angle is 180°.
Physical Properties of Alkynes
1. The first two members are gases next eight members (C5 – C12) are liquids and higher members are solids.
2. They are all colourless and odourless with the exception of acetylene which has slightly garlic odour due
to the presence of PH3 and H2S as impurities.
3. Alkynes are insoluble in water but soluble in organic solvents like ethers, carbon tetrachloride and
benzene.
4. Melting point, boiling point and density increase with increase in molar mass.

Chemical Properties of Alkynes

Alkynes show electrophilic as well as nucleophilic addition reactions.

(i) Acidic character of alkynes

(a) Addition of dihydrogen

(b) Addition of halogens