Introduction to Organic Chemistry
⚛️ Organic Chemistry Defined
- Chemistry of carbon compounds
- Carbon essential element (except: carbonates, cyanides, carbides, cyanates, oxides)
- Most contain H, O, N, halogens
- Millions of compounds known
- Complex molecules: proteins, enzymes, carbohydrates, lipids, vitamins, nucleic acids
🔗 Unique Properties of Carbon
- Catenation: Self-linking property → chains, rings
- Tetravalency: Forms 4 covalent bonds
- Small atomic size: Strong, short bonds
- Versatile bonding: Single, double, triple bonds
- Forms more compounds than all other elements combined
📐 Structural Formula
Definition: Shows atoms connected by bonds (lines)
Examples: C₂H₆ (ethane), CH₃Cl, CH₃OH, CH₃NH₂
Structural formula: Diagram showing atoms and bonds in molecule
11.1 Hydrocarbons
⛽ What are Hydrocarbons?
- Compounds containing only C and H
- Fuels: natural gas, LPG, CNG, petrol, diesel, kerosene
- Feedstock for: plastics, medicines, synthetic fibers, paints
🔬 Classification
| Type | Bond Type | General Formula | Example |
|---|---|---|---|
| Alkanes | Single bonds only | CₙH₂ₙ₊₂ | Methane CH₄ |
| Alkenes | Contains C=C | CₙH₂ₙ | Ethene C₂H₄ |
| Alkynes | Contains C≡C | CₙH₂ₙ₋₂ | Ethyne C₂H₂ |
| Aromatic | Benzene ring | CₙH₂ₙ₋₆ | Benzene C₆H₆ |
🔥 Methane – Simplest Hydrocarbon
11.3 Preparation of Alkanes
⚗️ 1. Cracking of Higher Hydrocarbons
Cracking Process
Higher hydrocarbons (less demand) → Smaller hydrocarbons (more demand)
Heat at ~500°C + Zeolite catalyst
⚡ 2. Reduction of Alkenes/Alkynes
Hydrogenation (Addition Reaction)
CH₂=CH₂ + H₂ → CH₃-CH₃ (Ni catalyst, 200°C)
CH≡CH + 2H₂ → CH₃-CH₃
- Hydrogenation: Adding H₂ to unsaturated compounds
- Catalyst: Nickel (Ni)
- Temperature: 200°C
- Application: Making banaspati ghee, margarine
🧪 3. Reduction of Alkyl Halides
Using Zn/HCl
Zn + 2HCl → ZnCl₂ + 2[H]
R-X + 2[H] → R-H + H-X
CH₃Cl + 2[H] → CH₄ + HCl
Alternative metal: Magnesium (Mg) can also be used
11.2 Alkanes (Saturated Hydrocarbons)
🔗 Characteristics
- Only C-C and C-H single bonds
- General formula: CₙH₂ₙ₊₂
- Fully saturated (all 4 carbon valencies used)
- Methane = parent hydrocarbon
- Low reactivity (distinguishing feature)
🏷️ IUPAC Nomenclature System
Longest chain carbon count
Class of compound (-ane)
Substituents & position
📊 Root Names (Table 11.1)
| Root | Carbon Atoms | Example |
|---|---|---|
| Meth- | 1 | CH₄ (Methane) |
| Eth- | 2 | C₂H₆ (Ethane) |
| Prop- | 3 | C₃H₈ (Propane) |
| But- | 4 | C₄H₁₀ (Butane) |
| Pent- | 5 | C₅H₁₂ (Pentane) |
| Hex- | 6 | C₆H₁₄ (Hexane) |
| Hept- | 7 | C₇H₁₆ (Heptane) |
| Oct- | 8 | C₈H₁₈ (Octane) |
| Non- | 9 | C₉H₂₀ (Nonane) |
| Dec- | 10 | C₁₀H₂₂ (Decane) |
🔍 Naming Example
Final name: 2-Methylbutane (iso-Butane)
n-Butane: CH₃-CH₂-CH₂-CH₃ (no branches)
✏️ From Textbook Exercises
Name: 2,3-Dimethylpentane
Longest chain: 5C (pentane)
Branches: Methyl at C2 & C3
Name: 2,2-Dimethylbutane
Longest chain: 4C (butane)
Branches: Two methyl groups at C2
⚛️ Electron Structures
H-C-H (tetrahedral)
H₃C-CH₃
H₃C-CH₂-CH₃
H₃C-CH₂-CH₂-CH₃
Methane: 0 methyl, 0 methylene
Ethane: 2 methyl (CH₃-), 0 methylene
Propane: 2 methyl, 1 methylene (-CH₂-)
Butane: 2 methyl, 2 methylene
Methyl: -CH₃ group
Methylene: -CH₂- group (between carbons)
Exercise Questions – Complete Solutions
Multiple Choice Questions:
ii) Which other metal can reduce alkyl halides?
Answer: (b) Mg
Detailed Explanation:
Alkyl halides can be reduced using:
1. Zinc (Zn) with HCl: Most common method
Zn + 2HCl → ZnCl₂ + 2[H] (nascent hydrogen)
R-X + 2[H] → R-H + H-X
2. Magnesium (Mg): Forms Grignard reagent intermediate
R-X + Mg → R-Mg-X (Grignard reagent)
R-Mg-X + H₂O → R-H + Mg(OH)X
Other options:
(a) Al – Not typically used for this reduction
(c) Ni – Catalyst for hydrogenation, not direct reduction of alkyl halides
(d) Co – Not standard for this reaction
iii) Naphtha combustion products?
Answer: (c) CO₂ and H₂O
Detailed Explanation:
Complete combustion of hydrocarbons:
Naphtha composition: Mixture of hydrocarbons (C₅-C₁₀)
Complete combustion: Hydrocarbon + excess O₂ → CO₂ + H₂O + heat
Incomplete combustion: If oxygen limited → CO + C (soot) + H₂O
Why not other options:
(a) Alkanes – Starting material, not product
(b) Alkenes – Intermediate in cracking, not combustion product
(d) Both – Incorrect, combustion gives oxides
v) Which alkane gives most heat when burnt?
Answer: (c) n-Butane
Detailed Explanation: Heat of combustion increases with carbon number:
| Alkane | Formula | Heat of Combustion (kJ/mol) |
|---|---|---|
| Methane | CH₄ | ~890 |
| Ethane | C₂H₆ | ~1560 |
| Propane | C₃H₈ | ~2220 |
| n-Butane | C₄H₁₀ | ~2878 |
| iso-Butane | C₄H₁₀ | ~2868 |
Trend: More carbons = more bonds = more heat released
n-Butane vs iso-Butane: n-Butane releases slightly more heat due to better packing/more efficient combustion
Among options: n-Butane (C₄) has most carbons → highest heat
vi) Which reaction not given by alkanes?
Answer: (c) Addition
Detailed Explanation:
Alkane reactions:
1. Substitution: ✓ Characteristic reaction (e.g., chlorination)
CH₄ + Cl₂ → CH₃Cl + HCl (with light)
2. Combustion: ✓ Burning with oxygen
CH₄ + 2O₂ → CO₂ + 2H₂O + heat
3. Cracking: ✓ Breaking larger alkanes into smaller ones
C₁₀H₂₂ → C₈H₁₈ + C₂H₄
4. Addition: ✗ NOT given by alkanes
• Alkanes are saturated (all single bonds)
• No double/triple bonds to add to
• Addition characteristic of alkenes/alkynes
Key point: Saturated = no addition reactions
vii) Hydrocarbon causing coal mine explosions?
Answer: (c) Methane
Detailed Explanation:
Coal mine gas (firedamp): Mainly methane (CH₄)
Why methane causes explosions:
1. Forms explosive mixture with air (5-15% CH₄ in air)
2. Released from coal seams during mining
3. Highly flammable, ignites easily
4. Complete combustion: CH₄ + 2O₂ → CO₂ + 2H₂O + heat
5. Rapid heat release causes pressure wave → explosion
Other hydrocarbons in mines: Ethane, propane (less common)
Safety measures: Ventilation, methane detectors, flame safety lamps
Historical: “Firedamp” explosions common in 19th/early 20th century mines
x) Oxygen moles to burn propane?
Answer: (b) 5 moles
Detailed Explanation:
Propane combustion equation:
Balancing steps:
1. Count C atoms: 3C → 3CO₂ (needs 3O₂ for CO₂)
2. Count H atoms: 8H → 4H₂O (needs 2O₂ for H₂O)
3. Total O₂: 3 (for CO₂) + 2 (for H₂O) = 5 O₂
Stoichiometry: 1 mol C₃H₈ : 5 mol O₂
Alternative method: General formula for alkane combustion:
CₙH₂ₙ₊₂ + (3n+1)/2 O₂ → nCO₂ + (n+1)H₂O
For propane (n=3): (3×3+1)/2 = (9+1)/2 = 10/2 = 5 O₂
Short Answer Questions:
i. Differentiate organic and inorganic compounds
Answer: Based on carbon content, bonding, properties, and sources.
• Contain carbon (essential)
• Covalent bonding
• Complex, large molecules
• Millions known
• From living organisms/synthesis
• Examples: CH₄, C₂H₅OH, proteins
• Usually flammable
• May/may not contain carbon
• Ionic/covalent bonding
• Simpler, smaller molecules
• Fewer in number
• From minerals/non-living
• Examples: NaCl, CO₂, H₂SO₄
• Usually non-flammable
Exceptions: Carbonates, cyanides, carbides, cyanates, CO, CO₂ classified as inorganic
ii. Why many organic compounds?
Answer: Due to carbon’s unique properties: catenation, tetravalency, multiple bonding.
Detailed reasons:
1. Catenation: Carbon forms strong C-C bonds
• Chains of any length: C-C-C-C-C…
• Branched chains: C-C-C, C-C-C
• Rings: C-C-C (cyclopropane)
2. Tetravalency: Forms 4 covalent bonds
• With H, O, N, halogens, other C
• Single, double, triple bonds
3. Isomerism: Same formula, different structures
• C₄H₁₀: n-butane & iso-butane
4. Multiple functional groups: -OH, -COOH, -NH₂, etc.
Result: More carbon compounds than all other elements combined
iv. How naphtha decomposed to lower hydrocarbons?
Answer: By cracking process: heating at high temperature with catalyst.
Detailed process:
Fractional distillation of petroleum → naphtha
Heat naphtha to ~500°C
Zeolite catalyst breaks C-C bonds
Chemical changes:
• Large hydrocarbons (C₁₀-C₁₈) → smaller (C₅-C₁₀)
• Some alkanes → alkenes + smaller alkanes
• C-C bonds break, new bonds form
Example: C₁₀H₂₂ → C₈H₁₈ + C₂H₄
Purpose: Convert less useful heavy fractions to more valuable fuels (petrol, diesel)
v. Iso-butane formulas
Answer: Three different formula representations
Explanation:
Molecular formula: Shows atom types and numbers (C₄H₁₀)
Structural formula: Shows atom connections and bonds
Condensed formula: Shows groups without drawing all bonds (CH₃)₃CH
Note: Same molecular formula as n-butane but different structure
vi. Usefulness of organic compounds
Answer: Essential for life, industry, medicine, and daily needs.
| Application | Examples | Importance |
|---|---|---|
| Fuels | Natural gas, petrol, diesel | Energy for transport, heating |
| Food | Carbohydrates, proteins, fats | Nutrition, energy source |
| Medicines | Antibiotics, painkillers | Healthcare, disease treatment |
| Clothing | Cotton, polyester, nylon | Textiles, fashion |
| Plastics | PVC, polyethylene | Packaging, construction |
| Agriculture | Fertilizers, pesticides | Food production |
| Cosmetics | Perfumes, creams | Personal care |
| Cleaning | Soaps, detergents | Hygiene |
vii. Five natural organic compounds
Answer: From plants, animals, and natural sources
Note: All biomolecules are organic compounds found naturally
Constructed Response Questions:
i. Why alkanes show little reactivity?
Answer: Due to strong sigma bonds, non-polar nature, and saturation.
Detailed reasons:
1. Strong C-C and C-H sigma bonds:
• Bond energies: C-C (347 kJ/mol), C-H (413 kJ/mol)
• High energy required to break bonds
2. Non-polar molecules:
• C and H have similar electronegativity (C=2.5, H=2.1)
• Bonds almost non-polar → no charged sites for attack
3. Saturation:
• All single bonds (sigma bonds)
• No pi bonds (weaker, more reactive)
• No sites for addition reactions
4. Lack of functional groups:
• Only C-C and C-H bonds
• No -OH, -COOH, -NH₂ etc. to react
5. Inert towards common reagents:
• Don’t react with acids, bases, oxidizing agents at room temp
• Only react under extreme conditions (high temp, light, catalysts)
Exception: Combustion (with O₂) and substitution (with halogens + light)
ii. Why natural gas + air explodes?
Answer: Methane forms explosive mixture with air (5-15% CH₄), rapid combustion causes pressure wave.
Detailed explanation:
Methane leaks into air
Forms explosive mixture (5-15% CH₄)
Ignition source (spark, flame)
Chemical reaction:
Why explosion occurs:
1. Rapid combustion releases heat quickly
2. Gases (CO₂, H₂O vapor) expand rapidly
3. Creates pressure wave (shock wave)
4. Damages surroundings
Explosive limits:
• Lower Explosive Limit (LEL): 5% CH₄ in air
• Upper Explosive Limit (UEL): 15% CH₄ in air
Below 5%: Too little fuel, won’t ignite
Above 15%: Too rich, insufficient oxygen
iii. Compare MP/BP of organic vs inorganic
Answer: Organic compounds generally have lower MP/BP than inorganic compounds.
• Lower MP/BP
• Covalent bonding
• Weak intermolecular forces
• Molecular crystals
• Examples:
• Methane: BP -161°C
• Ethanol: BP 78°C
• Glucose: MP 146°C
• Higher MP/BP
• Ionic bonding
• Strong electrostatic forces
• Ionic/covalent networks
• Examples:
• NaCl: MP 801°C
• SiO₂: MP 1713°C
• CaCO₃: MP 825°C
Reasons for difference:
Organic: Weak van der Waals forces between molecules
Inorganic: Strong ionic bonds or covalent networks
Exceptions: Some organic polymers have high MP (nylon: 263°C)
Trend in organic: MP/BP increases with molecular size
Descriptive Questions:
i. Importance of organic compounds in daily life
Answer: Essential for all aspects of modern life from food to technology.
| Area | Importance | Specific Examples |
|---|---|---|
| Food & Agriculture | Nutrition, food production | Carbohydrates, proteins, fats, fertilizers, pesticides |
| Clothing | Textiles, fashion | Cotton, wool, silk, polyester, nylon |
| Shelter | Construction materials | Wood, paints, varnishes, plastics, adhesives |
| Health | Medicine, healthcare | Drugs, antibiotics, vitamins, disinfectants |
| Transport | Fuels, materials | Petrol, diesel, rubber tires, plastic parts |
| Communication | Electronics, packaging | Plastics in devices, paper, ink |
| Entertainment | Sports, arts | Synthetic fibers in sports gear, paints, musical instruments |
| Personal Care | Hygiene, cosmetics | Soaps, shampoos, perfumes, creams |
Without organic compounds: No life (all biomolecules organic), no modern civilization
ii. Why whole branch based on carbon?
Answer: Carbon’s unique properties enable vast diversity of compounds forming basis of life.
Detailed reasons:
1. Versatile bonding:
• Forms 4 covalent bonds (tetravalent)
• Single, double, triple bonds possible
• Bonds with itself and many other elements
2. Catenation (self-linking):
• Forms chains of any length (C-C-C-C…)
• Branched chains and rings
• No other element does this to same extent
3. Small size & strong bonds:
• Small atomic radius → short, strong bonds
• C-C bond energy 347 kJ/mol (very strong)
• Forms stable compounds
4. Multiple bonding:
• Forms σ and π bonds
• Allows diverse structures: alkanes, alkenes, alkynes, aromatics
5. Isomerism:
• Same formula, different structures
• Millions of possible compounds
6. Basis of life:
• All biomolecules contain carbon
• DNA, proteins, carbohydrates, lipids
• Life as we know it is carbon-based
Result: More carbon compounds than all other elements combined
v. Usefulness of alkane combustion
Answer: Provides energy for transportation, heating, electricity, and industry.
Chemical basis: Combustion releases large amount of energy
Heat values: Methane: 890 kJ/mol, Propane: 2220 kJ/mol
Advantages: High energy density, relatively clean (compared to coal), easy to transport/store
Disadvantage: Produces CO₂ (greenhouse gas)
Investigative Question:
i. Natural gas explosion in kitchen – reason & prevention
Answer: Methane accumulates, forms explosive mixture, prevention through ventilation and safety devices.
Reason for explosion:
Gas valve left open
Methane leaks, spreads (lighter than air)
Forms explosive mixture (5-15% CH₄)
Ignition sources: Spark from switch, flame, static electricity
Rapid combustion: CH₄ + 2O₂ → CO₂ + 2H₂O + heat (explosion)
How to avoid:
1. Never leave gas valve open: Close when not in use
2. Check for leaks: Use soap solution on connections
3. Ventilation: Open windows, exhaust fans
4. Install gas detectors: Alarms for methane leaks
5. Safe ignition: Light match before opening gas
6. Regular maintenance: Check pipes, connections
7. No naked flames: If smell gas, don’t switch lights
8. Emergency: Know how to shut off main supply
Why spreads quickly: Methane less dense than air (16 g/mol vs 29 g/mol for air)
Safety first: If gas smell detected, evacuate, don’t use electrical switches, call emergency