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Hydrocarbons are classified as alkanes (Cₙₙ₊{2}, saturated, ), alkenes (Cₙₙ, one C=C, ), and alkynes (Cₙₙ₋{2}, one C≡C, sp), each with distinct hybridization and reactivity.
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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.
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Stability order for butane is anti > gauche > eclipsed > fully eclipsed, encoded by the mnemonic "A Gentle Evening Falls."
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Free radical halogenation of alkanes proceeds in three steps — initiation ( → 2X• by UV/heat), propagation (chain), and termination (radical combination) — with H-abstraction selectivity following 3° > 2° > 1°.
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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.
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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.
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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.
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Reductive ozonolysis (/Zn/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).
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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.
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Internal alkynes are selectively reduced to cis-alkenes by Lindlar's catalyst (syn-addition) or to trans-alkenes by Na/liquid (anti-addition via radical anion mechanism), with complete reduction to alkane requiring undeactivated /Pd–C.
Part of OC-02 — Hydrocarbons: Alkanes, Alkenes & Alkynes
Hydrocarbons: The 10-Sentence Summary
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