Nomenclature Common: named as if derived from hydrogen halide, H–X
Nomenclature Common: named as if derived from hydrogen halide, H–X CH 3 –Cl methyl chloride
Nomenclature Common: named as if derived from hydrogen halide, H–X CH 3 –Cl methyl chloride (CH 3 ) 2 CH–Br isopropyl bromide Br
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
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
Nomenclature IUPAC: named as substituted alkanes substituent name for X is halo
Nomenclature IUPAC: named as substituted alkanes substituent name for X is halo R–X haloalkane
Nomenclature IUPAC: named as substituted alkanes substituent name for X is halo R–X haloalkane F
Nomenclature IUPAC: named as substituted alkanes substituent name for X is halo R–X haloalkane 3-fluoroheptane F
Nomenclature IUPAC: named as substituted alkanes substituent name for X is halo R–X haloalkane 3-fluoroheptane F F
Nomenclature IUPAC: named as substituted alkanes substituent name for X is halo R–X haloalkane 3-fluoroheptane F ( S )-3-fluoroheptane F
Nomenclature IUPAC: named as substituted alkanes substituent name for X is halo R–X haloalkane 3-fluoroheptane F ( S )-3-fluoroheptane F
Nomenclature IUPAC: named as substituted alkanes substituent name for X is halo R–X haloalkane 3-fluoroheptane F ( S )-3-fluoroheptane F
Nomenclature IUPAC: named as substituted alkanes substituent name for X is halo R–X haloalkane 3-fluoroheptane F ( S )-3-fluoroheptane F Br
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
Some essential properties of haloalkanes • R–X are polar H δ− δ + C X H H
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 •
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
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
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
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
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
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
Recommend
More recommend