Unit 14: Hydrocarbons (8 Teaching Hours)
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Saturated Hydrocarbons (Alkanes)
- Preparation of Alkanes
- From Haloalkanes
- Reduction: Haloalkanes reduced with Zn/HCl or H₂/Pd (e.g., CH₃Cl + H₂ → CH₄ + HCl).
- Wurtz Reaction: Two haloalkanes with Na in dry ether (e.g., 2CH₃Br + 2Na → C₂H₆ + 2NaBr).
- Decarboxylation
- Sodium salt of carboxylic acid with soda lime (NaOH + CaO) (e.g., CH₃COONa + NaOH → CH₄ + Na₂CO₃).
- Catalytic Hydrogenation of Alkene and Alkyne
- Alkenes/alkynes with H₂ using Ni/Pt/Pd catalyst (e.g., C₂H₄ + H₂ → C₂H₆, C₂H₂ + 2H₂ → C₂H₆).
- Figure 1: Catalytic Hydrogenation (Diagram showing hydrogenation of ethene to ethane).
- From Haloalkanes
- Chemical Properties of Alkanes
- Substitution Reactions
- Halogenation: With halogens (e.g., Cl₂) in UV light (e.g., CH₄ + Cl₂ → CH₃Cl + HCl).
- Nitration: With conc. HNO₃ at high temperature (e.g., C₂H₆ + HNO₃ → C₂H₅NO₂ + H₂O).
- Sulphonation: With conc. H₂SO₄ or SO₃ (e.g., C₂H₆ + SO₃ → C₂H₅HSO₃).
- Figure 2: Halogenation of Methane (Diagram showing substitution of CH₄ with Cl₂).
- Oxidation of Ethane
- Complete combustion: 2C₂H₆ + 7O₂ → 4CO₂ + 6H₂O.
- Controlled oxidation: With MoO₃ catalyst, forms acetaldehyde or ethanol.
- Substitution Reactions
- Preparation of Alkanes
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Alkenes
- Preparation of Alkenes
- Dehydration of Alcohol
- Alcohol with conc. H₂SO₄ at 140–180°C (e.g., C₂H₅OH → C₂H₄ + H₂O).
- Dehydrohalogenation
- Haloalkane with alcoholic KOH (e.g., CH₃CH₂Br + KOH(alc) → C₂H₄ + KBr + H₂O).
- Catalytic Hydrogenation of Alkyne
- Alkyne with H₂ and Lindlar’s catalyst (Pd/CaCO₃) (e.g., C₂H₂ + H₂ → C₂H₄).
- Figure 3: Dehydration of Ethanol (Diagram showing dehydration of ethanol to ethene).
- Dehydration of Alcohol
- Chemical Properties of Alkenes
- Addition Reactions
- With HX (Markovnikov’s Addition): Adds H to carbon with more H atoms (e.g., C₃H₆ + HBr → CH₃CHBrCH₃).
- Peroxide Effect: In presence of peroxide, anti-Markovnikov addition (e.g., C₃H₆ + HBr(peroxide) → CH₃CH₂CH₂Br).
- With H₂O: Acid-catalyzed hydration forms alcohol (e.g., C₂H₄ + H₂O → C₂H₅OH).
- With O₃: Ozonolysis forms carbonyl compounds (e.g., C₂H₄ + O₃ → 2HCHO).
- With H₂SO₄: Forms alkyl hydrogen sulphate (e.g., C₂H₄ + H₂SO₄ → C₂H₅HSO₄).
- Figure 4: Markovnikov’s Addition (Diagram showing addition of HBr to propene).
- Addition Reactions
- Preparation of Alkenes
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Alkynes
- Preparation of Alkynes
- From Carbon and Hydrogen
- Electric arc between carbon electrodes in H₂ atmosphere (e.g., 2C + H₂ → C₂H₂).
- From 1,2-Dibromoethane
- Dehydrohalogenation with alcoholic KOH (e.g., CH₂BrCH₂Br + 2KOH(alc) → C₂H₂ + 2KBr + 2H₂O).
- From Chloroform/Iodoform
- Reaction with Ag powder (e.g., 2CHI₃ + 6Ag → C₂H₂ + 6AgI).
- Figure 5: Preparation of Ethyne (Diagram showing dehydrohalogenation of 1,2-dibromoethane).
- From Carbon and Hydrogen
- Chemical Properties of Alkynes
- Addition Reactions
- With H₂: Forms alkene, then alkane (e.g., C₂H₂ + H₂ → C₂H₄, C₂H₄ + H₂ → C₂H₆).
- With HX: Forms vinyl halide, then gem-dihalide (e.g., C₂H₂ + HBr → CH₂=CHBr, CH₂=CHBr + HBr → CH₃CHBr₂).
- With H₂O: Forms aldehyde/ketone (e.g., C₂H₂ + H₂O → CH₃CHO with HgSO₄/H₂SO₄).
- Acidic Nature
- Action with Sodium: Forms sodium acetylide (e.g., C₂H₂ + 2Na → Na₂C₂ + H₂).
- Action with Ammoniacal AgNO₃: Forms white precipitate (e.g., C₂H₂ + 2AgNO₃ → Ag₂C₂↓ + 2HNO₃).
- Action with Ammoniacal Cu₂Cl₂: Forms red precipitate (e.g., C₂H₂ + Cu₂Cl₂ → Cu₂C₂↓ + 2HCl).
- Figure 6: Acidic Nature of Ethyne (Diagram showing precipitate formation with AgNO₃).
- Addition Reactions
- Preparation of Alkynes
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Test of Unsaturation (Ethene & Ethyne)
- Bromine Water Test
- Ethene/Ethyne decolorizes red-brown Br₂ water by addition (e.g., C₂H₄ + Br₂ → C₂H₄Br₂).
- Baeyer’s Test
- Ethene/Ethyne decolorizes alkaline KMnO₄ (purple) forming glycols (e.g., C₂H₄ + H₂O + [O] → C₂H₆O₂).
- Figure 7: Bromine Water and Baeyer’s Test (Diagram showing decolorization of Br₂ and KMnO₄).
- Bromine Water Test
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Comparative Studies of Physical Properties of Alkane, Alkene, and Alkyne
- Physical Properties
- Boiling/Melting Points: Increase with molecular weight; alkanes > alkenes > alkynes (due to stronger van der Waals in alkanes).
- Solubility: Insoluble in water, soluble in non-polar solvents; alkanes least reactive, alkynes most polar.
- Density: Increases with carbon chain length; alkanes > alkenes > alkynes.
- Figure 8: Physical Properties Comparison (Diagram comparing boiling points of C₂H₆, C₂H₄, C₂H₂).
- Physical Properties
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Kolbe’s Electrolysis Methods for Preparation of Alkane, Alkene, and Alkyne
- Kolbe’s Electrolysis
- Electrolysis of sodium/potassium salts of carboxylic acids.
- Alkane: From sodium acetate (e.g., 2CH₃COONa + 2H₂O → C₂H₆ + 2CO₂ + 2NaOH + H₂).
- Alkene: From salts of unsaturated acids (e.g., fumarate yields C₂H₄).
- Alkyne: From salts of dicarboxylic acids (e.g., oxalate yields C₂H₂).
- Figure 9: Kolbe’s Electrolysis (Diagram showing electrolysis setup for ethane preparation).
- Kolbe’s Electrolysis