1) Basics of Organic Chemistry

  • Organic compounds: hydrocarbons and their derivatives.
  • Vital force theory: Organic compounds formed only in living systems (Berzelius).
  • Wöhler synthesis: Urea prepared from inorganic salts — disproved vital force theory.
  • Classification: Aliphatic / Cyclic → Saturated / Unsaturated → Aromatic / Alicyclic.

2) Aromaticity (Hückel Rule)

  • Aromatic compounds are planar, cyclic, conjugated.
  • Must obey (4n + 2) π electrons.
  • Show electrophilic substitution and resist addition.
  • Examples: Benzene (6π), Naphthalene (10π).
  • Heteroaromatics: Pyridine, Pyrrole, Furan, Thiophene.

3) Nomenclature Rules (Quick Recap)

  • Lowest locant rule: first substituent gets lowest number.
  • Lowest sum rule: lowest total of substituent positions.
  • First point of difference: lower number at first mismatch preferred.
  • Substituents written in alphabetical order.
  • Complex substituents written in brackets and numbered separately.

4) Functional Group Priority (High → Low)

–COOH > –SO3H > Anhydride > Ester > Acid chloride > Amide > –CN > –CHO > >C=O > –OH > –NH2 > C=C > C≡C > Halo / Nitro / Alkyl

5) Structural Isomerism

  • Chain isomerism: different carbon skeleton.
  • Positional isomerism: different position of bond or group.
  • Functional isomerism: different functional groups.
  • Metamerism: different alkyl groups on either side of same functional group.
  • Ring-chain isomerism: open chain vs cyclic structure.
  • Tautomerism: dynamic equilibrium (e.g., keto–enol).

6) Tautomerism

  • Interconversion due to shift of H-atom and π-electrons.
  • Keto–enol tautomerism: aldehydes & ketones with α-hydrogen.
  • β-diketones show higher enol content due to chelation.
  • Also seen in nitro–aci and nitroso–oxime systems.

7) Electronic Effects

Inductive Effect (I)

  • Permanent effect through σ-bonds.
  • –I groups: –NO2, –COOH, –F, –Cl, –Br.
  • +I groups: Alkyl groups.

Mesomeric Effect (M)

  • Delocalisation of π-electrons.
  • +M: –OH, –OR, –NH2 (ortho/para directors).
  • –M: –NO2, –CHO, –COOH (meta directors).

Electromeric Effect (E)

  • Temporary effect in presence of attacking reagent.
  • Occurs in compounds with π-bonds.

8) Resonance

  • Delocalisation of electrons in conjugated systems.
  • Actual structure is a resonance hybrid.
  • More resonance → more stability.
  • Bond order = average of resonating structures.
  • All resonating structures must have same atomic positions.

9) Reaction Intermediates

Free Radicals

  • Formed by homolytic cleavage.
  • sp² hybridised, highly reactive.
  • Stability: 3° > 2° > 1° > methyl.

Carbocations

  • Formed by heterolytic cleavage.
  • Electron deficient.
  • Stability: 3° > 2° > 1° > methyl.

Carbanions

  • Electron rich species.
  • Stability increases with electron-withdrawing groups.

Carbenes

  • Incomplete octet.
  • Exist as singlet or triplet.

10) Types of Organic Reactions

  • Addition: electrophilic, nucleophilic, radical.
  • Elimination: α, β, γ eliminations.
  • Substitution: SN, SR, SE reactions.
  • Condensation: two molecules combine with loss of small molecule.
  • Rearrangement: carbon skeleton rearranges.
  • Polymerisation: monomers → polymers.
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