
Classify mono halogen derivatives of alkanes by carbon hybridization, highlighting sp2 aryl halides and sp alkynyl halides, with benzyl halide and aryl halide examples and primary secondary tertiary context.
Explore the nomenclature of haloarenes, comparing common names with UPC/IUPAC naming, including ortho, meta, and para positions and symmetry considerations.
Explain methods to prepare haloalkanes from alcohols, detailing primary, secondary, and tertiary alcohols reacting with thionyl chloride under heat (or with catalysts) to form alkyl chlorides, with water as byproduct.
Explore the chlorination of alkanes under UV light, where chlorine substitutes hydrogen in a free radical mechanism to yield chloromethane, methylene chloride, chloroform, and carbon tetrachloride.
Learn how alkyl halides react with kcn or agcn in alcoholic solvent to form alkyl nitriles via substitution, with examples like methyl chloride becoming methyl cyanide.
Explore the SN2 mechanism in haloalkanes, illustrated by alkaline hydrolysis of methyl bromide, showing a concerted, single-step substitution where the nucleophile attacks as the C-Br bond breaks.
This lecture explains the SN2 mechanism: backside nucleophile attack, concerted bond breaking and forming, formation of the transition state, and 100 percent inversion of configuration.
The lecture presents the SN1 mechanism as a two-step process: carbocation formation, then nucleophile attack, highlighting electron-deficient, planar carbocation allowing attack from either side.
Explain the SN1 energy profile diagram, mapping reactants to a carbocation intermediate and final products through two transition states, highlighting activation energies e1 and e2 and delta H.
Explore optical activity in halogen derivatives, distinguishing ordinary light, monochromatic light, and plane polarized light. Explain how a Nicol prism, made from calcite, converts light to plane polarized form.
Explore the preparation of tetrahalogen derivatives of alkanes, focusing on carbon disulfide–chlorine reactions to give carbon tetrachloride, its water reactions forming phosgene, and its applications.
SUMMARY
Alkyl/ Aryl halides may be classified as mono, di, or polyhalogen (tri-, tetra-, etc.) compounds depending on whether they contain one, two or more halogen atoms in their structures. Since halogen atoms are more electronegative than carbon, the carbonhalogen bond of alkyl halide is polarised; the carbon atom bears a partial positive charge, and the halogen atom bears a partial negative charge.
Alkyl halides are prepared by the free radical halogenation of alkanes, addition of halogen acids to alkenes, replacement of –OH group of alcohols with halogens using phosphorus halides, thionyl chloride or halogen acids. Aryl halides are prepared by electrophilic substitution to arenes. Fluorides and iodides are best prepared by halogen exchange method.
The boiling points of organohalogen compounds are comparatively higher than the corresponding hydrocarbons because of strong dipole-dipole and van der Waals forces of attraction. These are slightly soluble in water but completely soluble in organic solvents.
The polarity of carbon-halogen bond of alkyl halides is responsible for their nucleophilic substitution, elimination and their reaction with metal atoms to form organometallic compounds. Nucleophilic substitution reactions are categorised into SN1 and SN2 on the basis of their kinetic properties. Chirality has a profound role in understanding the reaction mechanisms of SN1 and SN2 reactions. SN2 reactions of chiral alkyl halides are characterised by the inversion of configuration while SN1 reactions are characterised by racemisation.
A number of polyhalogen compounds e.g., dichloromethane, chloroform, iodoform, carbon tetrachloride, freon and DDT have many industrial applications. However, some of these compounds cannot be easily decomposed and even cause depletion of ozone layer and are proving environmental hazards.