Part of OC-02 — Hydrocarbons: Alkanes, Alkenes & Alkynes

Hydrocarbons: The 10-Sentence Summary

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  1. Hydrocarbons are classified as alkanes (CₙH2H_{2}ₙ₊{2}, saturated, sp3sp^{3}), alkenes (CₙH2H_{2}ₙ, one C=C, sp2sp^{2}), and alkynes (CₙH2H_{2}ₙ₋{2}, one C≡C, sp), each with distinct hybridization and reactivity.

  2. In alkane conformational analysis using Newman projections, the anti conformation of butane (180° dihedral) is most stable, and the fully eclipsed conformation (0° dihedral) is least stable because both methyl groups eclipse each other.

  3. Stability order for butane is anti > gauche > eclipsed > fully eclipsed, encoded by the mnemonic "A Gentle Evening Falls."

  4. Free radical halogenation of alkanes proceeds in three steps — initiation (X2X_{2} → 2X• by UV/heat), propagation (chain), and termination (radical combination) — with H-abstraction selectivity following 3° > 2° > 1°.

  5. Br2Br_{2} is the most selective halogen in free radical halogenation because Br• has higher activation energy for H abstraction, making it highly discriminating between C–H bond types.

  6. Markovnikov's rule governs ionic electrophilic addition of HX to alkenes: H adds to the carbon with more H atoms, forming the more stable carbocation intermediate.

  7. Anti-Markovnikov addition (Kharasch effect) occurs ONLY with HBr + organic peroxide — not with HCl (endothermic radical step) or HI (premature termination) — giving the regioisomeric product.

  8. Reductive ozonolysis (O3O_{3}/Zn/H2H_{2}O) cleaves the C=C bond, converting each doubly-bonded carbon to a carbonyl group (aldehyde if the carbon has H; ketone if it has no H).

  9. Terminal alkynes are more acidic than alkenes and alkanes because the sp-hybridized C–H bond has 50% s-character, and the resulting acetylide anion is stabilized by this high electronegativity of the sp carbon.

  10. Internal alkynes are selectively reduced to cis-alkenes by Lindlar's catalyst (syn-addition) or to trans-alkenes by Na/liquid NH3NH_{3} (anti-addition via radical anion mechanism), with complete reduction to alkane requiring undeactivated H2H_{2}/Pd–C.

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