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Unformatted text preview: S N 1 and S N 2 reactions of alkyl halides Introduction The two primary mechanisms for substitution reactions are the S N 1 and S N 2 reactions. Today we will be studying these reactions for all of the compounds shown below. You should work in pairs today. One of you can do all the S N 1 reactions and the other one can do all the S N 2 reactions. 2-bromobutane Cl Cl Ag + Br Cl Cl Br 1-chlorobutane 1-bromobutane Cl 1-chloro-2-butene 2-chloro-2-methyl propane 1-chloro-2-methyl propene A G D B E F C R-X NaI acetone OH R-I + NaX R-X O 1-chloro-2-methylpropane R R + + AgX S N 2: S N 1: 2-chlorobutane Cl H To test the S N 2 reactions we will use a solution of NaI in acetone. Acetone is an aprotic solvent that is fairly polar and I- is a reasonable nucleophile. If a reaction occurs, we will form Br- or Cl- , both of which will combine with the Na + to form either NaBr or NaCl. NaI is soluble in acetone, while NaCl and NaBr are not soluble and will form a precipitate. So if you see any precipitate, it indicates that the S N 2 reaction has occurred. More precipitate means more reaction....
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