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Purification & Elemental Analysis of Organic Compounds

CBSE Class 11 & JEE Mains • Module 04 of 20 • Knowing What You Have and How Pure It Is

📍 Chapter Overview

Purification & Analysis — Mind Map

Topics Covered: Criteria of Purity (BP, MP, Rf) · Methods of Purification (crystallisation, distillation, sublimation, chromatography) · Qualitative Analysis — Lassaigne's Sodium Fusion Test · Quantitative Analysis — Liebig's (C & H), Dumas (N), Kjeldahl (N), Carius (S, X), Victor Meyer (mol. mass)

🤖 AI Prompt — Mind Map: Detailed chemistry mind map on dark teal-navy gradient background. Central node: "Purification & Analysis of Organic Compounds" (white, bold). Five radiating branches: (1) "Criteria of Purity" — sharp melting/boiling point, single spot on TLC; (2) "Purification Methods" — icons: flask (crystallisation), condenser (distillation), funnel (chromatography), sublimation apparatus; (3) "Lassaigne's Sodium Fusion" — shows Na + compound → fusion → NaCN, Na₂S, NaX → colour tests: Prussian blue for N, lead acetate for S, AgNO₃ for halogens; (4) "Quantitative Analysis" — formulas box: %C = (12/44)×(mass CO₂/mass compound)×100, %N Kjeldahl formula, %S Carius formula; (5) "Chromatography" — column, TLC, paper — Rf = distance solute/distance solvent. Use bright teal, golden yellow and electric blue color scheme. Educational poster style, high resolution.

1. Criteria and Methods of Purity

A pure compound has a sharp, well-defined melting point (for solids) and boiling point (for liquids). Any impurity causes:

Chromatographic purity: A single spot on TLC (thin-layer chromatography) with a single, consistent Rf value confirms purity.

2. Methods of Purification

2.1 Crystallisation

Principle: Dissolve the impure solid in minimum hot solvent → cool slowly → the desired compound crystallises out (impurities remain in solution).

Solvent selection: The compound must be soluble in the hot solvent but sparingly soluble when cold. Common solvents: water, ethanol, acetone.

Fractional crystallisation: Used when two compounds have similar solubility — repeated crystallisation separates them.

Example: Purification of crude naphthalene from coal tar using hot ethanol. Cooling → pure naphthalene crystals form.

2.2 Distillation (Simple, Fractional, Steam)

Distillation Apparatus — Simple Distillation Setup
Draw a labeled diagram of a simple distillation apparatus for purifying a liquid organic compound. Components (all clearly labeled with arrows): (1) Round-bottomed flask with liquid mixture being heated on a wire gauze / heating mantle; (2) Thermometer inserted through rubber stopper at the neck of the flask, bulb at the side arm level; (3) Liebig condenser — a glass tube within a glass jacket, with cold water inlet at bottom and outlet at top (counterflow cooling); (4) Receiver / collection flask (conical flask or round-bottomed flask) at the end of the condenser; (5) Boiling chips in the flask to prevent bumping. Show arrows indicating vapor path: liquid → vapor in flask → through side arm → condenses in condenser → distillate collected. Add a temperature gauge on thermometer. The whole setup is clean, labeled in a science textbook style. White background, neat lines, proper scientific illustration quality.

Simple Distillation: Separates liquids with significantly different boiling points (>25°C difference) or separates a liquid from dissolved solids.

Fractional Distillation: Liquids with close boiling points (e.g., ethanol BP 78°C and water BP 100°C). Uses a fractionating column. Petroleum refining uses fractional distillation.

Steam Distillation: For compounds that decompose at their boiling point but are immiscible with water. The compound distils with steam at a temperature lower than 100°C. Example: Aniline (BP 184°C) is steam-distilled at ~98°C because it is slightly volatile and immiscible with water. Principle: total vapour pressure = Pcompound + Pwater = atmospheric pressure → mixture boils below 100°C.

Distillation under reduced pressure (vacuum distillation): For high-boiling or heat-sensitive compounds. Lowering pressure lowers boiling point.

2.3 Sublimation

Some solids convert directly to vapour (no liquid phase) when heated — they sublime. On cooling, the pure vapour solidifies.

Used for: Camphor, iodine, naphthalene, anthracene, benzoic acid, ammonium chloride.

Apparatus: A porcelain dish with the impure substance. Covered with an inverted funnel. Gentle heating → pure sublimate collects on the funnel walls.

2.4 Chromatography

Principle: Separation based on differential distribution between two phases — a stationary phase (silica, alumina, paper) and a moving phase (solvent, mobile phase). Different compounds travel different distances based on their affinity to each phase.

TLC (Thin Layer Chromatography) — Diagram with Rf Calculation
Draw a labeled TLC (thin layer chromatography) diagram. Show a rectangular TLC plate (silica on aluminum sheet). At the bottom, a clearly marked baseline with three spots: left spot = pure standard compound A, center spot = mixture to be analyzed, right spot = pure standard compound B. A solvent front line at the top of the plate. The spots have traveled different distances: compound A spot has moved 3 cm from baseline; compound B spot has moved 5 cm; mixture shows two spots at exactly 3cm and 5cm (confirming the mixture contains A and B). The solvent front is at 7 cm. Add calculation: "Rf of A = 3/7 = 0.43, Rf of B = 5/7 = 0.71". Label: "Rf = distance traveled by spot / distance traveled by solvent front". Show a beaker below the plate with solvent (mobile phase). Stationary phase = silica. Add arrows pointing to: "baseline", "solvent front", "spots", "Rf measurement". White background, neat labeled diagram, educational chemistry style.

Types of Chromatography:

Rf = Distance moved by substance / Distance moved by solvent front (always <1)

3. Qualitative Analysis — Lassaigne's Sodium Fusion Test

Purpose: To detect the presence of N, S, and halogens (Cl, Br, I) in an organic compound.

Principle: Alkali metals (Na) when fused with the organic compound at high temperature convert the covalently bonded elements into their ionic (water-soluble) forms that can then be tested.

Lassaigne's Sodium Fusion — Flow Diagram of All Tests
Create a detailed chemistry flow diagram for Lassaigne's Sodium Fusion Test on a white background. Top box: "Organic compound + Na metal → heated strongly in fusion tube (sodium fusion extract, SFE) → dissolved in distilled water → filtered". Then show four branching arrows going down from "SFE": Branch 1 (NITROGEN): "SFE + FeSO₄ (aq) + FeCl₃ → acidify with HCl → Prussian blue/green precipitate (Berlin blue, Fe₄[Fe(CN)₆]₃) forms → NITROGEN CONFIRMED. Equation: Na+C+N → NaCN; NaCN+FeSO₄→Na₄[Fe(CN)₆]; Na₄[Fe(CN)₆]+FeCl₃→Fe₄[Fe(CN)₆]₃↓ (Prussian blue)". Branch 2 (SULPHUR): "SFE + lead acetate solution → black precipitate of PbS → SULPHUR CONFIRMED. Or: SFE + Na₂[Fe(CN)₅NO] → deep violet/purple colour". Branch 3 (HALOGEN): "SFE + dilute HNO₃ + AgNO₃ → if white ppt (AgCl) → Cl present; pale yellow ppt (AgBr) → Br present; yellow ppt (AgI) → I present. Note: must acidify with HNO₃ first to destroy any CN⁻ and S²⁻ (avoid false positives)". Branch 4 (BOTH N AND S): "SFE + Na₂[Fe(CN)₅NO] → Blood red colour → BOTH N AND S present as NaSCN". Each branch in a different color box (pink for N, yellow for S, green for Cl, purple for N+S). White background, educational labeled flowchart quality.

Why must we acidify with HNO₃ before Halogen test?

SFE may contain CN⁻ and S²⁻ (from N and S in the compound). These also precipitate with Ag⁺ forming AgCN (white) and Ag₂S (black) — which would give false positives for the halogen test. Acidifying with HNO₃ first destroys CN⁻ and S²⁻ ions.

HCN gas and H₂S gas are evolved → removed → then AgNO₃ test is reliable for halogens only.

4. Quantitative Analysis — Elemental Estimation

4.1 Estimation of Carbon and Hydrogen — Liebig's Method

Principle: The organic compound is burned completely in excess O₂. C → CO₂ (absorbed in KOH), H → H₂O (absorbed in anhydrous CaCl₂ / Mg(ClO₄)₂). The increase in weights of the absorbents gives mass of CO₂ and H₂O formed.

Carbon:

%C = (12/44) × (mass of CO₂ / mass of compound) × 100

Hydrogen:

%H = (2/18) × (mass of H₂O / mass of compound) × 100

Derivation logic: 44g CO₂ contains 12g C. So (12/44) converts mass of CO₂ to mass of C. Similarly, 18g H₂O contains 2g H.

4.2 Estimation of Nitrogen

Dumas Method

Principle: Organic compound + CuO (oxidising) → heated → all N → N₂ gas (collected over KOH solution which absorbs CO₂). Volume of N₂ measured at room temperature and pressure.

%N = (28 × V × P) / (22400 × W) × 100

Where V = volume of N₂ at STP (in mL), P = corrected pressure, W = mass of compound in grams. At STP: 22400 mL N₂ = 28g N.

Kjeldahl's Method

Principle: Compound + conc. H₂SO₄ → digested → N → (NH₄)₂SO₄. Boil with NaOH → NH₃ released. NH₃ collected in excess H₂SO₄ (standard). Back-titrate excess H₂SO₄ with standard NaOH → volume used → calculate N%.

NOT applicable for: Compounds with N in nitro (–NO₂), azo (–N=N–), pyridine ring (N in non-amine forms). These don't convert to (NH₄)₂SO₄ quantitatively.

%N = (1.4 × M × V) / W

Where M = molarity of H₂SO₄ used, V = volume of H₂SO₄ (mL) neutralised by NH₃, W = mass of compound (g). (Factor 1.4 = 14/10 from unit conversions.)

4.3 Estimation of Sulphur and Halogens — Carius Method

Principle: Compound + fuming HNO₃ → oxidised in sealed Carius tube (heated to 250°C in a furnace) → S → BaSO₄ (if Ba²⁺ is added) → Halogen → AgX precipitate.

%S = (32/233) × (mass of BaSO₄ / mass of compound) × 100

Derivation: 233g BaSO₄ contains 32g S.

%Cl = (35.5/143.5) × (mass of AgCl / mass of compound) × 100
%Br = (80/188) × (mass of AgBr / mass of compound) × 100
%I = (127/235) × (mass of AgI / mass of compound) × 100

4.4 Estimation of Oxygen

Oxygen is NOT directly estimated by any standard method. It is calculated by difference:

%O = 100 − (%C + %H + %N + %S + %halogen)

4.5 Determination of Molecular Formula from Percentages

Step 1 — Find Empirical Formula: Divide % by atomic mass of each element. Divide all by the smallest quotient → gives simple whole number ratio → Empirical Formula.

Step 2 — Find Molecular Formula: Determine molecular mass (by Victor Meyer method, mass spectrometry etc.). Molecular Formula = n × Empirical Formula where n = Molecular mass / Empirical formula mass.

Example: A compound gives %C = 40%, %H = 6.7%, %O = 53.3%.

Moles: C = 40/12 = 3.33, H = 6.7/1 = 6.7, O = 53.3/16 = 3.33

Divide by smallest (3.33): C:H:O = 1:2:1 → Empirical formula = CH₂O

If mol. mass = 60g/mol → n = 60/30 = 2 → Molecular formula = C₂H₄O₂ (acetic acid or glycolaldehyde)

Worked Examples

Ex 1 M: 0.30g of an organic compound on Liebig's combustion gives 0.44g CO₂ and 0.18g H₂O. Find %C and %H.

Solution:
%C = (12/44) × (0.44/0.30) × 100 = (0.2727) × (1.467) × 100 = 40%
%H = (2/18) × (0.18/0.30) × 100 = (0.1111) × (0.60) × 100 = 6.67%


Ex 2 M: In Kjeldahl's method, 0.50g compound liberates NH₃ that neutralises 25 mL of 0.1M H₂SO₄. Find %N.

Solution:
%N = (1.4 × M × V) / W = (1.4 × 0.1 × 25) / 0.50 = 3.5/0.50 = 7%


Ex 3 H: A compound has %C = 75%, %H = 25%, mol. mass = 16. Find molecular formula.

Solution: Moles: C = 75/12 = 6.25, H = 25/1 = 25. Divide by 6.25: C:H = 1:4. Empirical formula = CH₄. Empirical mass = 16. n = 16/16 = 1. Molecular formula: CH₄ (methane).

Practice Problems

E Q1. What colour precipitate forms in Lassaigne's test when compound contains nitrogen? Name the compound formed.

E Q2. Why can't Kjeldahl's method be used for compounds containing −NO₂ groups?

M Q3. 0.20g compound on combustion gives 0.33g CO₂ and 0.135g H₂O. Find %C and %H. If %O = 53.3%, find empirical formula.

M Q4. An organic compound (0.40g) on Carius method gives 0.58g AgCl. Find %Cl.

H Q5. A compound contains C, H, and S. On analysis: %C = 24.4, %H = 4.1, %S = remaining. Mol. mass = 98. Find empirical and molecular formula. (Assume remaining = %S). [H₂SO₄ has mol. mass 98 and contains S = 32.7%]

  1. Using %H = 1/18 (hydrogen ratio) instead of 2/18 in Liebig's formula — water has 2 H per molecule.
  2. Forgetting to acidify with HNO₃ before halogen AgNO₃ test — results in false positives from CN⁻ and S²⁻.
  3. Applying Kjeldahl's for pyridine or −NO₂ compounds — it doesn't work for ring-N or nitro-N.
  4. Using molecular weight for empirical formula — find empirical ratio first using moles, then use mol. mass to find n.
  5. Computing %O by direct method — there is no direct method for O. Always: %O = 100 − (sum of others).
EstimationMethodFormula
%CLiebig combustion12/44 × mass CO₂ / mass compound × 100
%HLiebig combustion2/18 × mass H₂O / mass compound × 100
%NDumas28 × V(N₂ at STP) / 22400 × mass compound × 100
%NKjeldahl1.4 × M × V / W
%SCarius32/233 × mass BaSO₄ / mass compound × 100
%ClCarius35.5/143.5 × mass AgCl / mass compound × 100
%OBy difference100 − (%C + %H + %N + %S + %X)
Purification MethodUsed When
CrystallisationSolid + impurities; solubility difference with temperature
Simple distillationLiquids with BP difference >25°C or liquid + solid
Fractional distillationLiquids with close boiling points
Steam distillationHigh-BP compounds immiscible with water; heat-sensitive
SublimationCamphor, iodine, naphthalene; sublime directly
Chromatography (TLC)Small quantities; Rf for ID; monitor reactions