Stage 1: IUPAC & Structural Isomerism 3-4 Days
Functional Group Priority Order 1-2 Qs
Sequence: -COOH > -SO3H > -COOR > -COCl > -CONH2 > -CN > -CHO > >C=O > -OH > -NH2 > C=C > C≡C
Polyfunctional naming: principal suffix chooses longest chain containing maximum unsaturation
Structural Isomerism & Stereocenters
Chain vs Position vs Functional vs Metamerism (ethers, 2° amines, esters)
Tautomerism: Keto-Enol stability order (aromatic enol in phenol, active methylene enolization)
Geometrical (cis/trans & E/Z) & Optical: Chiral C, Enantiomers, Diastereomers, Meso forms
Stage 2: GOC — General Organic Chemistry 8-10 Days
4 Electronic Displacement Effects 3-4 Qs
Inductive (+I vs -I): distance dependent (dead after C3); -NO2 > -CN > -COOH > -F > -Cl > -Br > -I
Mesomeric (+M / -M): lone pair delocalization vs electron withdrawing groups on benzene
Hyperconjugation (Baker-Nathan): count α-hydrogens; controls alkene & carbocation stability
Electromeric (E-effect): temporary polarizability under attacking reagent influence
Intermediates & Carbocation Shifts
Stability Hierarchy: Tropylium > Cyclopropylmethyl > Benzyl ≈ Allyl > 3° > 2° > 1° > Methyl
Rearrangement: 1,2-Hydride shift (2° → 3°) and 1,2-Methyl shift (adjacent quaternary C)
Aromaticity Checklist (Hückel): Cyclic + Planar + Conjugated + (4n+2) π electrons
Stage 3: Hydrocarbons (Alkane, Alkene, Alkyne) 5-6 Days
Addition Traps & Cleavage 2-3 Qs
Markovnikov addition (carbocation pathway); rearrangement occurs with HX
Peroxide Effect (Kharasch): ONLY with HBr (free radical). HCl and HI NEVER show peroxide effect!
Ozonolysis: O3, Zn/H2O gives aldehydes/ketones (reductive); O3, H2O2 oxidizes aldehydes to acids
Alkyne Hydration: HgSO4/dil. H2SO4 forms enol → tautomerizes to ketone (ethyne gives acetaldehyde)
Stage 4: Haloalkanes, Haloarenes & Alcohols 7-8 Days
SN1 vs SN2 & E1 vs E2 Matrix 2-3 Qs
SN1: 3° > 2° > 1°, two steps, carbocation intermediate, racemization, polar protic solvent (H2O, EtOH)
SN2: 1° > 2° > 3°, single step, backside attack, Walden inversion, polar aprotic solvent (acetone, DMSO)
Elimination: Saytzeff (more substituted) with small base; Hofmann (less substituted) with bulky t-BuOK
Williamson Ether: R-X (must be 1°) + R'-O⁻Na⁺. If 3° R-X is used, 100% alkene forms (E2 trap)!
Stage 5: Aldehydes, Ketones & Carboxylic Acids 4-5 Qs (40% Weight)
Carbonyl Reactivity & Condensation Must Master
Nucleophilic Addition: HCHO > R-CHO > R-CO-R (steric hindrance + +I reduces electrophilicity)
Aldol Condensation: requires α-H; dil. NaOH → β-hydroxy aldehyde → heat → α,β-unsaturated carbonyl
Cannizzaro Reaction: NO α-H (HCHO, PhCHO); conc. KOH → disproportionation (alcohol + salt)
Carbonyl Reductions: Clemmensen (Zn-Hg/conc. HCl) vs Wolff-Kishner (NH2NH2/KOH/glycol, Δ)
HVZ Reaction: Carboxylic acid with α-H + Br2/Red P → α-bromo carboxylic acid
Stage 6: Amines, Diazonium & Biomolecules 5-6 Days
Amine Syntheses & Azo Couplings 3-4 Qs
Gabriel Phthalimide: PURE 1° aliphatic amines only. Aryl halides & 3° halides DO NOT react!
Hoffmann Bromamide: R-CONH2 + Br2 + 4KOH → R-NH2 (1 less carbon amine! 4 moles of base)
Hinsberg Test: Benzenesulfonyl chloride; 1° amine gives alkali-soluble ppt, 2° alkali-insoluble, 3° no reaction
Diazonium Salts (0-5°C): Sandmeyer (Cu2Cl2/HCl) vs Gattermann (Cu/HCl) vs Balz-Schiemann (HBF4 → Ar-F)
Azo Coupling: Ar-N2+Cl- + Phenol (pH 9-10) → Orange Dye; + Aniline (pH 4-5) → Yellow Dye