Organic Chemistry – Chapter 11 Revision Tool | EverExams

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
📝 Memorization Tip: “Organic = Carbon compounds (except C-oxides, carbonates, cyanides, carbides)”

🔗 Unique Properties of Carbon

Catenation: C-C-C-C chains
Tetravalency: 4 covalent bonds
Small size: strong bonds
  • 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

Methane: CH₄
Structural: H-C-H
Condensed: CH₄

Definition: Shows atoms connected by bonds (lines)

Examples: C₂H₆ (ethane), CH₃Cl, CH₃OH, CH₃NH₂

🔍 From Textbook Exercise:

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

TypeBond TypeGeneral FormulaExample
AlkanesSingle bonds onlyCₙH₂ₙ₊₂Methane CH₄
AlkenesContains C=CCₙH₂ₙEthene C₂H₄
AlkynesContains C≡CCₙH₂ₙ₋₂Ethyne C₂H₂
AromaticBenzene ringCₙH₂ₙ₋₆Benzene C₆H₆

🔥 Methane – Simplest Hydrocarbon

Methane: CH₄
Uses: Fuel, H₂ gas, carbon black
Produces: CS₂, CHCl₃, HCN
💡 Key Point: This chapter focuses only on Alkanes (saturated hydrocarbons)

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

Naphtha (mixture) → Alkanes + Alkenes (C₅ to C₁₀)
🎯 Why cracking? Balances petroleum supply with demand for fuels

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

Step 1: Root
Longest chain carbon count
Step 2: Suffix
Class of compound (-ane)
Step 3: Prefix
Substituents & position

📊 Root Names (Table 11.1)

RootCarbon AtomsExample
Meth-1CH₄ (Methane)
Eth-2C₂H₆ (Ethane)
Prop-3C₃H₈ (Propane)
But-4C₄H₁₀ (Butane)
Pent-5C₅H₁₂ (Pentane)
Hex-6C₆H₁₄ (Hexane)
Hept-7C₇H₁₆ (Heptane)
Oct-8C₈H₁₈ (Octane)
Non-9C₉H₂₀ (Nonane)
Dec-10C₁₀H₂₂ (Decane)

🔍 Naming Example

CH₃-CH-CH₂-CH₃
CH₃
1. Longest chain: 4C → But-
2. Class: Alkane → -ane
3. Branch: Methyl at C2

Final name: 2-Methylbutane (iso-Butane)

n-Butane: CH₃-CH₂-CH₂-CH₃ (no branches)

✏️ From Textbook Exercises

(i) CH₃-CH-CH-CH₂-CH₃

Name: 2,3-Dimethylpentane

Longest chain: 5C (pentane)

Branches: Methyl at C2 & C3

(ii) CH₃-C-CH₂-CH₃

Name: 2,2-Dimethylbutane

Longest chain: 4C (butane)

Branches: Two methyl groups at C2

⚛️ Electron Structures

Methane (CH₄):
H-C-H (tetrahedral) Ethane (C₂H₆):
H₃C-CH₃ Propane (C₃H₈):
H₃C-CH₂-CH₃ Butane (C₄H₁₀):
H₃C-CH₂-CH₂-CH₃
📊 Methyl & Methylene Groups:

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:

CₙH₂ₙ₊₂ + (3n+1)/2 O₂ → nCO₂ + (n+1)H₂O

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:

AlkaneFormulaHeat of Combustion (kJ/mol)
MethaneCH₄~890
EthaneC₂H₆~1560
PropaneC₃H₈~2220
n-ButaneC₄H₁₀~2878
iso-ButaneC₄H₁₀~2868

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:

C₃H₈ + 5O₂ → 3CO₂ + 4H₂O

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.

Organic Compounds:
• Contain carbon (essential)
• Covalent bonding
• Complex, large molecules
• Millions known
• From living organisms/synthesis
• Examples: CH₄, C₂H₅OH, proteins
• Usually flammable Inorganic Compounds:
• 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:

Step 1:
Fractional distillation of petroleum → naphtha
Step 2:
Heat naphtha to ~500°C
Step 3:
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

Molecular Formula: C₄H₁₀
Structural Formula:
CH₃-CH-CH₃
CH₃
Condensed Formula: (CH₃)₃CH

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.

ApplicationExamplesImportance
FuelsNatural gas, petrol, dieselEnergy for transport, heating
FoodCarbohydrates, proteins, fatsNutrition, energy source
MedicinesAntibiotics, painkillersHealthcare, disease treatment
ClothingCotton, polyester, nylonTextiles, fashion
PlasticsPVC, polyethylenePackaging, construction
AgricultureFertilizers, pesticidesFood production
CosmeticsPerfumes, creamsPersonal care
CleaningSoaps, detergentsHygiene

vii. Five natural organic compounds

Answer: From plants, animals, and natural sources

1. Glucose: C₆H₁₂O₆ (sugar in fruits) 2. Cellulose: (C₆H₁₀O₅)ₙ (plant cell walls) 3. Starch: (C₆H₁₀O₅)ₙ (food storage in plants) 4. Protein: Made of amino acids (meat, eggs) 5. Fats/Oils: Triglycerides (animal fat, vegetable oil) 6. DNA/RNA: Nucleic acids (genetic material) 7. Chlorophyll: C₅₅H₇₂O₅N₄Mg (photosynthesis) 8. Natural rubber: (C₅H₈)ₙ (from rubber trees)

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:

Step 1:
Methane leaks into air
Step 2:
Forms explosive mixture (5-15% CH₄)
Step 3:
Ignition source (spark, flame)

Chemical reaction:

CH₄ + 2O₂ → CO₂ + 2H₂O + 890 kJ/mol

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.

Organic Compounds:
Lower MP/BP
• Covalent bonding
• Weak intermolecular forces
• Molecular crystals
• Examples:
• Methane: BP -161°C
• Ethanol: BP 78°C
• Glucose: MP 146°C Inorganic Compounds:
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.

AreaImportanceSpecific Examples
Food & AgricultureNutrition, food productionCarbohydrates, proteins, fats, fertilizers, pesticides
ClothingTextiles, fashionCotton, wool, silk, polyester, nylon
ShelterConstruction materialsWood, paints, varnishes, plastics, adhesives
HealthMedicine, healthcareDrugs, antibiotics, vitamins, disinfectants
TransportFuels, materialsPetrol, diesel, rubber tires, plastic parts
CommunicationElectronics, packagingPlastics in devices, paper, ink
EntertainmentSports, artsSynthetic fibers in sports gear, paints, musical instruments
Personal CareHygiene, cosmeticsSoaps, 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.

Application Specific Use Alkanes Used Transportation Car, airplane, ship engines Petrol (C₅-C₁₀), diesel (C₁₂-C₁₈) Heating Home heating, cooking Natural gas (CH₄), LPG (C₃H₈/C₄H₁₀) Electricity Power generation Natural gas, fuel oil Industry Manufacturing processes Various hydrocarbon fuels Rocketry Space launch vehicles Kerosene (RP-1) with liquid oxygen

Chemical basis: Combustion releases large amount of energy

CₙH₂ₙ₊₂ + (3n+1)/2 O₂ → nCO₂ + (n+1)H₂O + Heat

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:

Step 1:
Gas valve left open
Step 2:
Methane leaks, spreads (lighter than air)
Step 3:
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:

Prevention Measures:

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