CNGNGE JOHN MCMURRY CHAPTER12 Organohalides: Nucleophilic Substitutions and Eliminations Organic Chemistry with Biological applications
CHAPTER12 Organohalides: Nucleophilic Substitutions and Eliminations
Alkyl Halides Alkyl halide or haloalkanes Compounds with a halogen atom bonded to a saturated sp3- hybridized carbon atom Widespread in nature Chloromethane is released in large amounts by ocean kelp,as well as by forest fires and volcanoes Vast array of industrial applications Use as inhaled anesthetics,refrigerants,pesticides,and solvents F Br H C三 F-C-C-H CI-C-F H-C-Br CI F CI CI H Trichloroethylene Halothane Dichlorodifluoromethane Bromomethane (a solvent) (an inhaled anesthetic) (a refrigerant) (a fumigant) Leang All Rights Reaorved
Alkyl halide or haloalkanes ▪ Compounds with a halogen atom bonded to a saturated sp3 - hybridized carbon atom ▪ Widespread in nature ▪ Chloromethane is released in large amounts by ocean kelp, as well as by forest fires and volcanoes ▪ Vast array of industrial applications ▪ Use as inhaled anesthetics, refrigerants, pesticides, and solvents Alkyl Halides
Alkyl Halides Other halo-substituted compounds are used as medicines and food additives Sucralose,marketed as Splenda,is 600 times as sweet as ordinary table sugar,sucrose CH2CI HOCH2 CI CH2CI HO HO Sucralose
Other halo-substituted compounds are used as medicines and food additives ▪ Sucralose, marketed as Splenda, is 600 times as sweet as ordinary table sugar, sucrose Alkyl Halides
Alkyl Halides Alkyl halides are not often involved in the biochemical pathways of terrestrial organisms The kinds of reactions they undergo-nucleophilic substitutions and eliminations -are frequently involved Alkyl halide chemistry acts as a relatively simple model for many mechanistically similar but structurally more complex reactions found in biomolecules
Alkyl halides are not often involved in the biochemical pathways of terrestrial organisms ▪ The kinds of reactions they undergo – nucleophilic substitutions and eliminations – are frequently involved ▪ Alkyl halide chemistry acts as a relatively simple model for many mechanistically similar but structurally more complex reactions found in biomolecules Alkyl Halides
12-1 Naming Alkyl Halides Haloalkanes 0 Commonly called alkyl halides 。 The halogen is treated as a substituent on a parent alkane chain Alkyl halides can be named by following three steps: Step 1 Find the longest chain,and name it as the parent 。 If a double or triple bond is present,it must be included in the parent chain
Haloalkanes • Commonly called alkyl halides • The halogen is treated as a substituent on a parent alkane chain Alkyl halides can be named by following three steps: Step 1 Find the longest chain, and name it as the parent • If a double or triple bond is present, it must be included in the parent chain 12-1 Naming Alkyl Halides