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Haloalkanes and Haloarenes — Class 12 CBSE Chemistry revision notes

A 5-page visual revision sheet for Haloalkanes and Haloarenes, written for Class 12 CBSE Chemistry. Formulas, diagrams and the traps that cost marks, laid out to be read the night before rather than the term before. Free, and it opens inside CapCompass.

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Haloalkanes and Haloarenes in one look

a halogen on carbon sets up a leaving group, and everything else follows from how well it leaves

Haloalkane vs haloarene

Haloalkane (alkyl halide)
  • halogen on an sp^3 carbon, e.g. CH_3CH_2Cl
  • C-X bond is a normal sigma bond, halogen lone pairs not delocalised
  • undergoes nucleophilic substitution readily
Haloarene (aryl halide)
  • halogen on an sp^2 aromatic carbon, e.g. chlorobenzene
  • halogen lone pair conjugates into the ring, C-X gets partial double-bond character
  • resists nucleophilic substitution under ordinary conditions, needs forcing conditions

Classification and nomenclature

  • primary (1°): halogen carbon attached to one other carbon; secondary (2°): two; tertiary (3°): three
  • allylic halide: halogen on the carbon next to a C=C double bond; benzylic halide: halogen on the carbon next to an aromatic ring
  • IUPAC name treats halogen as a substituent prefix: chloro, bromo, iodo, fluoro, cited alphabetically with other substituents
  • vinylic halide: halogen directly ON a double-bond carbon (C=C-X); like aryl halides, this C-X also resists substitution

Common preparation routes

  • from an alcohol, SOCl_2 (best: only gases as byproducts) R-OH+SOCl_2→ R-Cl+SO_2+HCl
  • from an alkene, HX addition (Markovnikov) R-CH=CH_2+HX→ R-CHX-CH_3
  • from an alkane, free-radical halogenation under UV light R-H+X_2to R-X+HX

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