Haloalkanes and Haloarenes

30 lessons, pages 2241–2270.

  1. Organohalogen Compounds — Classifying alkyl, allylic, benzylic and aryl halides
  2. Haloalkane Nomenclature — Naming monohalo and polyhalo saturated compounds
  3. Haloarene Nomenclature — Naming aryl halides and substituted benzene rings
  4. Carbon–Halogen Bond Polarity — Electronegativity, bond length and leaving-group behavior
  5. Physical Properties of Organohalides — Boiling points, density and solubility trends
  6. Preparation by Alcohol Halogenation — Converting alcohols to alkyl halides
  7. Preparation by Alkene Addition — Electrophilic addition of hydrogen halides and halogens
  8. Radical Halogenation of Alkanes — Chain substitution and product selectivity
  9. Preparation of Aryl Halides — Electrophilic aromatic halogenation and diazonium routes
  10. Nucleophilic Substitution Overview — Replacing a leaving group at saturated carbon
  11. SN2 Mechanism — Concerted backside attack and transition state
  12. SN2 Rate and Substrate Effects — Bimolecular rate law and steric hindrance
  13. SN2 Stereochemistry — Walden inversion at a reacting stereocenter
  14. SN1 Mechanism — Ionization to a carbocation followed by attack
  15. SN1 Rate and Carbocation Stability — Unimolecular rate law and substrate stabilization
  16. SN1 Stereochemistry and Rearrangement — Planar intermediates, product mixtures and shifts
  17. Leaving Groups and Nucleophiles — Distinguishing nucleophilicity from leaving-group ability
  18. Solvent Effects on Substitution — Polar protic and aprotic effects on SN1 and SN2
  19. Choosing SN1 or SN2 — Integrating substrate, nucleophile, solvent and rate evidence
  20. Elimination from Haloalkanes — Forming alkenes by loss of hydrogen halide
  21. E2 Mechanism — Concerted beta-proton removal and leaving-group departure
  22. E1 Mechanism — Carbocation formation followed by deprotonation
  23. Substitution versus Elimination — How substrate, base strength and temperature affect competition
  24. Alkene Regioselectivity in Elimination — Zaitsev and Hofmann product tendencies
  25. Optical Isomerism in Haloalkanes — Chiral carbon, enantiomers and optical activity
  26. Haloarene Bonding and Reactivity — Resonance, partial double-bond character and substitution resistance
  27. Substitution on Aromatic Halides — Activated nucleophilic aromatic substitution and its conditions
  28. Organometallic Formation from Halides — Grignard reagents and moisture-sensitive carbon–metal bonds
  29. Environmental and Safety Context — Persistent halogenated compounds and responsible handling
  30. Haloalkanes and Haloarenes Review — Synthesizing preparation, mechanisms and stereochemical outcomes