Ch_322a_6.022

Ch_322a_6.022 - As in all S N 2 reactions, these syntheses...

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Use of the S N 2 Reaction in Organic Synthesis The conversion of one compound into another through a chemical reaction is called synthesis . The S N 2 reaction is often used to convert alkyl halides into other functional groups. R- X for R= CH 3 , 1 o , 2 o X = Cl,Br, I Nucleophiles HO - R'O - HS - :CN - R'C C: - R'-C-O - O = R' 3 N: N 3 - R- OH alcohols R- OR' ethers R- SH thiols R- CN nitriles R C CR' alkynes R -O-C-R' O esters R- NR' 3 + ammonium ion R- N 3 azides
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Stereochemistry of S N 2 Synthetic Reactions
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Unformatted text preview: As in all S N 2 reactions, these syntheses proceed with inversion at a stereocenter . N C:-cyanide ion + C CH 3 CH 2 CH 3 H Br (R)-2-bromobutane C CH 2 CH 3 H CH 3 N C (S)-2-methylbutanenitrile Note: These synthetic reactions are limited to alkyl halides . Vinylic and aryl halides do not react readily by either the S N 1 or S N 2 mechanisms. C=C X vinylic halide X aryl halide...
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Ch_322a_6.022 - As in all S N 2 reactions, these syntheses...

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