SLIDE 1
Nomenclature Common: named as if derived from hydrogen halide, HX - - PowerPoint PPT Presentation
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
SLIDE 2
SLIDE 3
Br
Nomenclature Common: named as if derived from hydrogen halide, H–X CH3–Cl methyl chloride (CH3)2CH–Br isopropyl bromide
SLIDE 4
Br
Nomenclature Common: named as if derived from hydrogen halide, H–X CH3–Cl methyl chloride (CH3)2CH–Br isopropyl bromide R–X alkyl halide
SLIDE 5
Br
Nomenclature Common: named as if derived from hydrogen halide, H–X CH3–Cl methyl chloride (CH3)2CH–Br isopropyl bromide R–X alkyl halide grouped into 1E, 2E, 3E classes based on identity of R
SLIDE 6
Nomenclature IUPAC: named as substituted alkanes substituent name for X is halo
SLIDE 7
Nomenclature IUPAC: named as substituted alkanes substituent name for X is halo R–X haloalkane
SLIDE 8
F
Nomenclature IUPAC: named as substituted alkanes substituent name for X is halo R–X haloalkane
SLIDE 9
F
Nomenclature IUPAC: named as substituted alkanes substituent name for X is halo R–X haloalkane 3-fluoroheptane
SLIDE 10
F F
Nomenclature IUPAC: named as substituted alkanes substituent name for X is halo R–X haloalkane 3-fluoroheptane
SLIDE 11
F F
Nomenclature IUPAC: named as substituted alkanes substituent name for X is halo R–X haloalkane 3-fluoroheptane (S)-3-fluoroheptane
SLIDE 12
F F
Nomenclature IUPAC: named as substituted alkanes substituent name for X is halo R–X haloalkane 3-fluoroheptane (S)-3-fluoroheptane
SLIDE 13
F F
Nomenclature IUPAC: named as substituted alkanes substituent name for X is halo R–X haloalkane 3-fluoroheptane (S)-3-fluoroheptane
SLIDE 14
F F Br
Nomenclature IUPAC: named as substituted alkanes substituent name for X is halo R–X haloalkane 3-fluoroheptane (S)-3-fluoroheptane
SLIDE 15
F F Br
Nomenclature IUPAC: named as substituted alkanes substituent name for X is halo R–X haloalkane 3-fluoroheptane (S)-3-fluoroheptane (1R,3S)-1-bromo-3-methylcyclohexane
SLIDE 16
Some essential properties of haloalkanes
- R–X are polar
C X H H H δ+ δ−
SLIDE 17
Some essential properties of haloalkanes
- R–X are polar
- the C of C–X is intrinsically electrophilic. This dominates the chemistry of this functional group
C X H H H δ+ δ−
SLIDE 18
Some essential properties of haloalkanes
- R–X are polar
- 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
bp - 0.5 EC bp 79 EC
C X H H H δ+ δ−
Cl
SLIDE 19
Some essential properties of haloalkanes
- R–X are polar
- 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
bp - 0.5 EC bp 79 EC
- R–X are toxic
C X H H H δ+ δ−
Cl
SLIDE 20
Some essential properties of haloalkanes
- R–X are polar
- 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
bp - 0.5 EC bp 79 EC
- R–X are toxic
- R–X are relatively rare as natural products
C X H H H δ+ δ−
Cl
SLIDE 21
Cl Cl Cl Cl Cl OCH3 Cl Cl Cl O H CH3 O O Cl Cl OSO3 Cl OH Cl Cl Cl Cl OH Cl OH Cl Cl Cl OH OH
- Synthetic and Naturally Occurring Haloalkanes
DDT (insecticide) methyl ether of a trichloroorcinol LD50 = 115 mg/kg (fungicide produced by water lillies) cytotoxic sulfolipid from Mytilus galloprovincialis IC50 = 13 µM
SLIDE 22
Cl Cl Cl Cl Cl OCH3 Cl Cl Cl O H CH3 O O Cl Cl OSO3 Cl OH Cl Cl Cl Cl OH Cl OH Cl Cl Cl OH OH
- Synthetic and Naturally Occurring Haloalkanes
DDT (insecticide) methyl ether of a trichloroorcinol LD50 = 115 mg/kg (fungicide produced by water lillies) (compare LD50 acetaminophen = 338 mg/kg) cytotoxic sulfolipid from Mytilus galloprovincialis IC50 = 13 µM
SLIDE 23