bonding in alkyl halides. h alkyl halides are polar = 1.9 d h h c cl –––– ++++ dipole...
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alkyl halides are polar Dipole MomentsTRANSCRIPT
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Bonding in Alkyl Halides Bonding in Alkyl Halides
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HH
alkyl halides are polaralkyl halides are polar
= 1.9 D= 1.9 D
HH
HH
CC ClCl––++
Dipole MomentsDipole Moments
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alkyl halides are polaralkyl halides are polar
Dipole MomentsDipole Moments
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+ + – –
– – + +
+ + – – + + – – + + – –
Dipole-Dipole Attractive ForcesDipole-Dipole Attractive Forces
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+ + – –
– – + +
+ + – – + + – – + + – –
Dipole-Dipole Attractive ForcesDipole-Dipole Attractive Forces
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Boiling pointBoiling pointSolubility in waterSolubility in water
DensityDensity
Physical Properties of Physical Properties of Alkyl Halides:Alkyl Halides:
Intermolecular ForcesIntermolecular Forces
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4444 4848
-42-42 -32-32
00 1.91.9
CHCH33CHCH22CHCH33 CHCH33CHCH22FF
MolecularMolecularweightweight
BoilingBoilingpoint, °Cpoint, °C
DipoleDipolemoment, Dmoment, D
Effect of Structure on Boiling PointEffect of Structure on Boiling Point
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4444
--4242
00
CHCH33CHCH22CHCH33
MolecularMolecularweightweight
BoilingBoilingpoint, °Cpoint, °C
DipoleDipolemoment, Dmoment, D
Intermolecular forcesIntermolecular forcesare weak.are weak.
Only intermolecularOnly intermolecularforces are inducedforces are induceddipole-induced dipoledipole-induced dipoleattractions.attractions.
Effect of Structure on Boiling PointEffect of Structure on Boiling Point
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4848
-32-32
1.91.9
CHCH33CHCH22FF
MolecularMolecularweightweight
BoilingBoilingpoint, °Cpoint, °C
DipoleDipolemoment, Dmoment, D
A polar molecule;A polar molecule;therefore dipole-dipoletherefore dipole-dipoleand dipole-inducedand dipole-induceddipole forces contributedipole forces contributeto intermolecular to intermolecular attractions.attractions.
Effect of Structure on Boiling PointEffect of Structure on Boiling Point
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Boiling point increases with increasingBoiling point increases with increasingnumber of halogensnumber of halogens
CHCH33Cl Cl -24°C-24°C
CHCH22ClCl22 40°C40°C
CHClCHCl33 61°C61°C
CClCCl44 77°C77°C
CompoundCompound Boiling PointBoiling Point
Even though CClEven though CCl4 4 is the only compound in this list without is the only compound in this list without a dipole moment, it has the highest boiling point.a dipole moment, it has the highest boiling point.
Induced dipole-induced dipole forces are greatest in CClInduced dipole-induced dipole forces are greatest in CCl44 because it has the greatest number of Cl atoms. Cl is more because it has the greatest number of Cl atoms. Cl is more polarizable than H. polarizable than H.
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But trend is not followed when halogenBut trend is not followed when halogenis fluorineis fluorine
CHCH33CHCH22FF -32°C-32°C
CHCH33CHCHFF22 -25°C-25°C
CHCH33CCFF33 -47°C-47°C
CCFF33CCFF33 -78°C-78°C
CompoundCompound Boiling PointBoiling Point
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But trend is not followed when halogenBut trend is not followed when halogenis fluorineis fluorine
CHCH33CHCH22FF -32°C-32°C
CHCH33CHCHFF22 -25°C-25°C
CHCH33CCFF33 -47°C-47°C
CCFF33CCFF33 -78°C-78°C
CompoundCompound Boiling PointBoiling Point
Fluorine is not very polarizable and induced dipole-Fluorine is not very polarizable and induced dipole-induced dipole forces decrease with increasing induced dipole forces decrease with increasing fluorine substitution.fluorine substitution.
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Solubility in waterSolubility in water
Alkyl halides are insoluble in water.Alkyl halides are insoluble in water.
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DensityDensity
Alkyl fluorides and alkyl chlorides Alkyl fluorides and alkyl chlorides areareless dense than water.less dense than water.
Alkyl bromides and alkyl iodides are Alkyl bromides and alkyl iodides are more dense than water.more dense than water.