Classification and Nomenclature of Organic Halides


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Classification and Nomenclature of Organic Halides

  1. 1. CHAPTER 6 Presented By: Cyra Mae R. Soreda
  3. 3.  An organic compound containing at least one carbon-halogen bond (C-X)  X (F, Cl, Br, I) replaces H  Can contain many C-X bonds 3
  4. 4. Hydrocarbons can also contain other atoms, such as halogens (F, Cl, Br, I). Halogen atoms are treated like branching alkyl groups. Halogen Group Name F fluoro C chloro Br bromo I iodo
  5. 5.  An alkyl halide is classified according to the kind of carbon that bears the halogen.  Alkyl halides are classified into three classes:  Primary Alkyl Halide (Iº RX)  Secondary Alkyl Halide (2º RX)  Tertiary Alkyl Halide (3º RX)
  6. 6.  When one hydrogen atom of methyl group is replaced by an alkyl group, then the carbon of the substituted methyl is called Primary carbon atom. CH3-CH2-I (Ethyl iodide) For example:
  7. 7.  When two hydrogen atoms of methyl group are replace by any alkyl group, then the carbon atom of substituted methyl is called secondary carbon atom.. For example:
  8. 8.  When three hydrogen atoms of methyl groups are replaced by any alkyl group, then the carbon atom of the substituted methyl is calledTertiary carbon atom. For example:
  9. 9. CH3 CH CH3 Cl CH3CH2F (CH3)3CBr
  10. 10.  The two that are most widely used are:  SYSTEMATIC NAME (IUPAC name)  ALTERNATIVE NAME (common names)  Both types can be applied to alcohols and alkyl halides.
  11. 11.  Find and name the parent chain. As naming alkanes, select the longest chain as the parent chain.  Number the parent chain. Always number the chain beginning at the end nearer the first substituent, regardless of whether t is alkyl or halo. 12
  12. 12.  If more than one of the same kind of halogen is present, number each and use of the prefixes di-, tri-, tetra-, and so on. For example, 1,3-dichloro-3-methylbutane
  13. 13.  If different halogens are present, number each according to its position. List all substituents in alphabetical order .
  14. 14.  Begin at the end nearer the substituent whose name comes first in the alphabet 15
  15. 15.  Give names for the following: 16
  16. 16.  Give names for the following: 17 Iodobutane 1-chloro-3-methylbutane 1,5-dibromo-2,2-dimethylpentane 1,3-dichloro-3-methylbutane 1-chloro-3-ethyl-4-iodopentane 2-bromo-5-chlorohexane
  17. 17.  Treat halogen as parent with alkyl side group  Name as alkyl halide.  Useful only for small alkyl groups. 18
  18. 18.  The family called alkyl halides does not have a suffix.  Halides are always named as prefixes.  Fluorine is called “fluoro”  Chlorine is called “chloro”  Bromine is called “bromo”  Iodine is called “iodo”
  19. 19. Name the alkyl group and the halogen as separate words (alkyl + halide) CH3F CH3CH2CH2CH2CH2Cl CH3CH2CHCH2CH2CH3 Br H I
  20. 20.  Give names for the following: 21 butyl iodide) (isopentyl chloride) CH3 CH CH2CH3 Cl CH3 CH CH3 CH2F
  21. 21.  CH2X2 called methylene halide.  CHX3 is a haloform.  CX4 is carbon tetrahalide.  Examples:  CH2Cl2 is methylene chloride  CHCl3 is chloroform  CCl4 is carbon tetrachloride. => Chapter 6 22
  22. 22.  Geminal dihalide: two halogen atoms are bonded to the same carbon  Vicinal dihalide: two halogen atoms are bonded to adjacent carbons. C H H H C H Br Br geminal dihalide C H H Br C H H Br vicinal dihalide
  23. 23.  Solvents - degreasers and dry cleaning fluid  Reagents for synthesis of other compounds  Anesthetic: Halothane is CF3CHClBr  CHCl3 used originally (toxic and carcinogenic)  Freons, chlorofluorocarbons or CFC’s  Freon 12, CF2Cl2, now replaced with Freon 22, CF2CHCl, not as harmful to ozone layer.  Pesticides - DDT banned in U.S.
  24. 24.  Some uses: Fire-resistant solvents Refrigerants Pharmaceuticals and precursors