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Nomenclature Common: named as if derived from hydrogen halide, HX - PowerPoint PPT Presentation

Nomenclature Common: named as if derived from hydrogen halide, HX Nomenclature Common: named as if derived from hydrogen halide, HX CH 3 Cl methyl chloride Nomenclature Common: named as if derived from hydrogen halide, HX CH 3


  1. Nomenclature Common: named as if derived from hydrogen halide, H–X

  2. Nomenclature Common: named as if derived from hydrogen halide, H–X CH 3 –Cl methyl chloride

  3. Nomenclature Common: named as if derived from hydrogen halide, H–X CH 3 –Cl methyl chloride (CH 3 ) 2 CH–Br isopropyl bromide Br

  4. Nomenclature Common: named as if derived from hydrogen halide, H–X CH 3 –Cl methyl chloride (CH 3 ) 2 CH–Br isopropyl bromide Br R–X alkyl halide

  5. Nomenclature Common: named as if derived from hydrogen halide, H–X CH 3 –Cl methyl chloride (CH 3 ) 2 CH–Br isopropyl bromide Br R–X alkyl halide grouped into 1 E , 2 E , 3 E classes based on identity of R

  6. Nomenclature IUPAC: named as substituted alkanes substituent name for X is halo

  7. Nomenclature IUPAC: named as substituted alkanes substituent name for X is halo R–X haloalkane

  8. Nomenclature IUPAC: named as substituted alkanes substituent name for X is halo R–X haloalkane F

  9. Nomenclature IUPAC: named as substituted alkanes substituent name for X is halo R–X haloalkane 3-fluoroheptane F

  10. Nomenclature IUPAC: named as substituted alkanes substituent name for X is halo R–X haloalkane 3-fluoroheptane F F

  11. Nomenclature IUPAC: named as substituted alkanes substituent name for X is halo R–X haloalkane 3-fluoroheptane F ( S )-3-fluoroheptane F

  12. Nomenclature IUPAC: named as substituted alkanes substituent name for X is halo R–X haloalkane 3-fluoroheptane F ( S )-3-fluoroheptane F

  13. Nomenclature IUPAC: named as substituted alkanes substituent name for X is halo R–X haloalkane 3-fluoroheptane F ( S )-3-fluoroheptane F

  14. Nomenclature IUPAC: named as substituted alkanes substituent name for X is halo R–X haloalkane 3-fluoroheptane F ( S )-3-fluoroheptane F Br

  15. Nomenclature IUPAC: named as substituted alkanes substituent name for X is halo R–X haloalkane 3-fluoroheptane F ( S )-3-fluoroheptane F (1 R ,3 S )-1-bromo-3-methylcyclohexane Br

  16. Some essential properties of haloalkanes • R–X are polar H δ− δ + C X H H

  17. Some essential properties of haloalkanes • R–X are polar H δ− δ + C X H H the C of C–X is intrinsically electrophilic . This dominates the chemistry of this functional group •

  18. Some essential properties of haloalkanes • R–X are polar H δ− δ + C X H H the C of C–X is intrinsically electrophilic . This dominates the chemistry of this functional group • • R–X have bp’s higher than corresponding R–H Cl bp - 0.5 E C bp 79 E C

  19. Some essential properties of haloalkanes • R–X are polar H δ− δ + C X H H the C of C–X is intrinsically electrophilic . This dominates the chemistry of this functional group • • R–X have bp’s higher than corresponding R–H Cl bp - 0.5 E C bp 79 E C • R–X are toxic

  20. Some essential properties of haloalkanes • R–X are polar H δ− δ + C X H H the C of C–X is intrinsically electrophilic . This dominates the chemistry of this functional group • • R–X have bp’s higher than corresponding R–H Cl bp - 0.5 E C bp 79 E C • R–X are toxic • R–X are relatively rare as natural products

  21. Synthetic and Naturally Occurring Haloalkanes Cl Cl Cl Cl H O OCH 3 Cl Cl Cl Cl CH 3 DDT (insecticide) methyl ether of a trichloroorcinol LD 50 = 115 mg/kg (fungicide produced by water lillies) O - O Cl OSO 3 Cl OH Cl OH OH Cl OH Cl Cl Cl OH Cl Cl Cl Cl cytotoxic sulfolipid from Mytilus galloprovincialis IC 50 = 13 µ M

  22. Synthetic and Naturally Occurring Haloalkanes Cl Cl Cl Cl H O OCH 3 Cl Cl Cl Cl CH 3 DDT (insecticide) methyl ether of a trichloroorcinol LD 50 = 115 mg/kg (fungicide produced by water lillies) (compare LD 50 acetaminophen = 338 mg/kg) O - O Cl OSO 3 Cl OH Cl OH OH Cl OH Cl Cl Cl OH Cl Cl Cl Cl cytotoxic sulfolipid from Mytilus galloprovincialis IC 50 = 13 µ M

  23. OH Cl Cl O H O OH O HO O OH Cl sucralose (Splenda™) 400-800 times as sweet as sugar OH OH O OH H O H O O HO O OH OH sucrose

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