CHEM 227: CHAPTER 10
31 Cards in this Set
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Alkyl halide hybridization
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sp3
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bigger halogen = ___ bond
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longer
weaker
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IUPAC naming
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"fluoro"
number with substituent as 1
end in -ide
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Converting alkane to alkyl halide
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add X2
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converting alkene to alkyl halide
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add HX
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converting alkyne to alkyl halide
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add 2 HX
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Converting 1' alcohol to alkyl halide
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treat w/ PX3 or SOCl2
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Converting 2' alcohol to alkyl halide
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treat w/ PX3 or SOCl2
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Converting 3' alcohol to alkyl halide
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treat w/ HX
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Alcohol to alkyl halide mvmt of OH & X
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OH replaced with X
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Allylic carbon
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carbons bonded to carbons on double bond
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Allylic hydrogens
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Hs on allylic carbon
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Allylic bromination
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NBS reagent
adds Br to allylic C, replaces 1 allylic H with BR
yields 2 alkyl halides
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In allylic bromination, ___ products formed & they ____
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2
1 is just replaced, 1 moves double bond toward allylic C to get another allylic C
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In allylic bromination, brominate which allylic C?
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brominate poorer allylic C
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In allylic bromination, brominate which allylic C if equally poor
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just pick one
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Mechanism of bromination
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radical reaction with initiation, propagation, and termination
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In bromination, Br abstracts allylic Hs becaust
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allylic C-H bond weaker than other bonds
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Allylic radicals ___ stable than 1', 2', 3' radicals because
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more
resonance stabilizes, one pi bond forms and switches other
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Grignard Reagent
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R-Mg-X
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Preparing alkyl halide with Grignard reagent
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ether or THF
added to alkyl halide
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Reaction of Grignard reagent and alkyl halide
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Add Mg between C and X
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alkyl halide + H2O reaction
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alkyl halide + Grignard, add H2O -> alkane
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Oxidation
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adding NOX
removing H
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Reduction
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removing NOX
adding H
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deciding molecular oxidation or reduction
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-1 per H
+1 per NOX
increase = oxidation
decrease = reduction
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Molecule with higher oxidation # = ___ oxidized molecule
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most
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R-OH + PX3 ->
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R-X
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R-X + 2Li ->
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R-Li
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R-Li + CuX ->
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R-CuLi
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R-CuLi + R-X ->
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R + LiX
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CHEM 227: CHAPTER 9