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Chapter 6 handouts - Chapter 6 Alkyl Halides: Nucleophilic...

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Chapter 6 Alkyl Halides: Nucleophilic Substitution and Elimination
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Chapter 6 2 Classes of Halides • Alkyl: Halogen, X, is directly bonded to ___ carbon. • Vinyl: X is bonded to ___ carbon of ______. • Aryl: X is bonded to __ carbon on ______ ring. Examples: C H H H C H H Br alkyl halide CC H H H Cl vinyl halide I aryl halide
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Chapter 6 3 Polarity and Reactivity • Halogens are more ___________ than C. • Carbon-halogen bond is _____, so carbon has partial _________ charge. • Carbon can be attacked by a ________. • Halogen can leave with the ________ pair. C H H H Br δ + δ -
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Chapter 6 4 Classes of Alkyl Halides • _______ halides: only one C, CH 3 X • ________: C to which X is bonded has only one C-C bond. • ________: C to which X is bonded has two C-C bonds. • _________: C to which X is bonded has three C-C bonds.
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Chapter 6 5 Classify These: CH 3 3 Cl 3 2 F (CH 3 ) 3 CBr 3 I
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Chapter 6 6 Dihalides • ________ dihalide: two halogen atoms are bonded to the same carbon • _______ dihalide: two halogen atoms are bonded to adjacent carbons. C H H H C H Br geminal dihalide C H H C H H vicinal dihalide
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Chapter 6 7 IUPAC Nomenclature • Name as _________. • Choose the longest carbon chain, even if the _______________ to any of those C’s. • Use ___________ numbers for position. CH 3 2 3 Cl 3 (CH 2 ) 2 CH(CH 2 ) 2 3 2 2 Br
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Chapter 6 8 Systematic Common Names • Name as __________. • Useful only for ______ alkyl groups. • Name these: CH 3 2 3 Cl (CH 3 ) 3 CBr 3 3 2 F
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Chapter 6 9 “Trivial” Names •C H 2 X 2 called methylene halide. • CHX 3 is a haloform. X 4 is carbon tetrahalide. • Examples: ¾ CH 2 Cl 2 is ______________ ¾ CHCl 3 is ___________ ¾ CCl 4 is _____________.
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Chapter 6 10 Uses of Alkyl Halides • Solvents - degreasers and dry cleaning fluid • Reagents for synthesis of other compounds • Anesthetic: Halothane is CF 3 CHClBr ¾ CHCl 3 used originally (toxic and carcinogenic) • Freons, chlorofluorocarbons or CFC’s ¾ Freon 12, CF 2 Cl 2 , now replaced with Freon 22, CF 2 CHCl, not as harmful to ozone layer. • Pesticides - DDT banned in U.S. C H CCl 3 Cl Cl
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Chapter 6 11 Dipole Moments μ = 4.8 x δ x d , where δ is the charge (proportional to Δ EN) and d is the distance (bond length) in Angstroms. • Electronegativities: ______________ • Bond lengths: ___________________ • Bond dipoles: C-Cl > C-F > C-Br > C-I 1.56 D 1.51 D 1.48 D 1.29 D • Molecular dipoles depend on _______ , too!
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Chapter 6 12 Boiling Points • Greater intermolecular forces, _______ b.p. ¾ _____________ attractions not significantly different for different halides ¾ _____________ greater for larger atoms • Greater mass, _________ b.p.
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This note was uploaded on 04/08/2008 for the course CHEM 223 taught by Professor Pearson during the Fall '07 term at Case Western.

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Chapter 6 handouts - Chapter 6 Alkyl Halides: Nucleophilic...

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