Hydrocarbons Lec 001

Hydrocarbons
Presented by: Virda Aftab

Learning
Outcomes
Classification of Hydrocarbons
Reactivity of Alkanes
Shape of Ethane and Cyclopropane
Preparation of Alkenes
Classification of
Hydrocarbons
• Hydrocarbons are organic compounds composed entirely
of carbon and hydrogen atoms. They are classified based
on the type of bonding between the carbon atoms and the
structure of their carbon skeleton.
• Classification:
1- Open Chain HCs’ – Saturated and un-saturated
2- Closed chain HCs’ – Aliphatic and Aromatic
Classification of
Hydrocarbons
• Open-Chain Hydrocarbons
These hydrocarbons have a linear or branched structure. They do not form rings.
Saturated Hydrocarbons (Alkanes)
• Contain only single bonds between carbon atoms – Single covalent bond
• General formula: CₙH₂ₙ₊₂.
• Examples: Methane (CH₄), Ethane (C₂H₆), Propane (C₃H₈).
• Saturated hydrocarbons are relatively unreactive due to their stable C-C and C-
H single bonds.
• Each single bonded carbon is sp3 hybridized.
Classification of
Hydrocarbons
• Open-Chain Hydrocarbons
Unsaturated Hydrocarbons
• Contain one or more double or triple bonds between carbon atoms.
Subcategories:
• Alkenes: Contain at least one double bond. General formula: CₙH₂ₙ.
Example: Ethene (C₂H₄), Propene (C₃H₆).
• Alkynes: Contain at least one triple bond. General formula: CₙH₂ₙ₋₂.
Example: Ethyne (C₂H₂), Propyne (C₃H₄).
• Unsaturated hydrocarbons are more reactive than saturated hydrocarbons due to the
presence of double or triple bonds.
Classification of
Hydrocarbons
• Closed Chain Hydrocarbons:
These hydrocarbons form a cyclic structure by connecting the ends of the carbon chain.
• Alicyclic Hydrocarbons
Cyclic hydrocarbons that do not contain aromatic (benzene-like) rings.
Can be saturated or unsaturated.
General formula: Depends on the number of carbons in the ring.
• Saturated alicyclic hydrocarbons: Cycloalkanes (e.g., Cyclopropane, Cyclohexane).
• Unsaturated alicyclic hydrocarbons: Cycloalkenes (e.g., Cyclopentene, Cyclohexene).
Example: Cyclohexane (C₆H₁₂), Cyclopentene (C₅H₈).
Classification of
Hydrocarbons
• Closed Chain Hydrocarbons:
• Aromatic Hydrocarbons
Contain one or more benzene rings (planar rings with alternating single and double
bonds).
Highly stable due to resonance in the benzene ring.
General formula: C₆H₆ (Benzene) and derivatives.
Examples:
• Benzene (C₆H₆).
• Toluene (C₆H₅CH₃).
• Naphthalene (C₁₀H₈).
Classification of
Hydrocarbons
Alkanes are generally known to be unreactive due to their stable structure,
consisting of only single sigma (σ) bonds between carbon atoms (C–C) and carbon-
hydrogen atoms (C–H). However, they can undergo certain types of reactions,
mainly combustion and substitution.
Non-Polar Bonds
Alkanes have non-polar covalent bonds because the electronegativity difference
between carbon (C) and hydrogen (H) is minimal.
This non-polarity means alkanes do not easily interact with polar substances (e.g.,
water), making them hydrophobic.
Their low polarity and lack of significant functional groups contribute to their low
reactivity with most reagents.
Strength of Sigma (σ) Bonds

Alkanes have strong sigma bonds, both C–C and C–H, which require
considerable energy to break.
The C–C bond strength is about 348 kJ/mol, and the C–H bond strength is about
412 kJ/mol, which makes alkanes quite stable.
This bond strength is a key reason why alkanes are relatively inert and do not
react easily under normal conditions.
Free Radical Substitution of
Ethane
While alkanes are generally unreactive, they can undergo free radical
substitution reactions, especially in the presence of light or heat.
This reaction type involves the replacement of a hydrogen atom with another atom
(often a halogen) and proceeds through a free radical mechanism.
Example: Chlorination of Ethane
Steps in the Free Radical Substitution Reaction of Ethane with Chlorine

(Cl₂)
1- Initiation
2- Propagation
3- Termination
Ethane
Initiation:
When chlorine (Cl₂) is exposed to ultraviolet (UV) light, it dissociates into two
chlorine radicals.
Propagation:
The chlorine radical reacts with an ethane molecule, removing a hydrogen atom
and forming a methyl radical (C₂H₅·).
The ethyl radical then reacts with another Cl₂ molecule, creating chloroethane
(C₂H₅Cl) and another chlorine radical.
Ethane
Termination:
Two free radicals combine to form a stable molecule, stopping the chain reaction.
For example:
Shapes of Ethane and Cyclopropane
Ethane (C₂H₆)
Molecular Structure: Ethane has a simple open-chain structure with two carbon
atoms single-bonded to each other, and each carbon is bonded to three hydrogen
atoms.
Bonding and Shape:
The carbons in ethane have sp³ hybridization, meaning each carbon has four
single bonds (one C–C bond and three C–H bonds).
This results in a tetrahedral geometry around each carbon atom with bond
angles of approximately 109.5°.
Shape:
Ethane can rotate freely around the C–C sigma bond, giving it different
conformations. The most notable conformations are the staggered (more
stable) and eclipsed (less stable) conformations.
Overall, the structure of ethane is often visualized as a pair of connected
tetrahedra, with the molecule taking on a linear appearance from end to
end.
Ethane (C₂H₆)
Cyclopropane(C3H6)
Molecular Structure:
Cyclopropane is a cyclic molecule with three carbon atoms bonded in a ring, and
each carbon is bonded to two hydrogen atoms.
Bonding and Shape:
Cyclopropane also has sp³ hybridized carbon atoms, which would ideally form 109.5°
bond angles, typical for sp³ bonds.
However, because the three carbon atoms form a triangle (three-membered ring), the
bond angles are forced to 60°, far less than the ideal tetrahedral angle. This creates
significant angle strain (or ring strain) in the molecule.
Shape:
Cyclopropane forms a triangular planar shape, with all three carbon atoms in the
same plane.
The strain from the 60° bond angles makes cyclopropane highly reactive compared to
larger, less-strained ring structures.
Cyclopropane(C3H6)
Dehydration of Alcohols
Reaction: In this process, an alcohol loses a water molecule to form an alkene.
Conditions:
• A strong acid catalyst such as concentrated sulfuric acid (H₂SO₄) or
phosphoric acid (H₃PO₄) is used.
• Heat is applied (typically around 170°C for sulfuric acid).
Mechanism:
• Step 1: Protonation – The hydroxyl (OH) group in the alcohol is protonated
by the acid catalyst, making it a better leaving group (water, H₂O).
• Step 2: Formation of a Carbocation – The protonated hydroxyl group leaves,
creating a carbocation (a positively charged carbon intermediate).
• Step 3: Elimination – A hydrogen atom is removed from an adjacent carbon
atom, leading to the formation of a double bond (C=C) and producing the
alkene.
Dehydrohalogenation of Halogenoalkanes (Alkyl Halides)

Reaction: This reaction removes a hydrogen halide (HX, where X is a halogen)
from a halogenoalkane to form an alkene.
Conditions:
• A strong base such as potassium hydroxide (KOH) in ethanol is used.
• Heating the mixture helps drive the reaction.
Mechanism:
• Step 1: The base (OH⁻) abstracts a proton (H⁺) from a carbon atom
adjacent to the one bonded to the halogen.
• Step 2: This elimination creates a double bond (C=C) between the two
carbons, and the halide ion (X⁻) leaves, resulting in the formation of an
alkene.

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Hydrocarbons

Presented by: Virda Aftab

Strength of Sigma (σ) Bonds

Steps in the Free Radical Substitution Reaction of Ethane with Chlorine

Dehydrohalogenation of Halogenoalkanes (Alkyl Halides)

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