Lecture25-notes - Chapter 9 Reading 9.1-9.9 Practice...

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10/26/09 1 Chapter 9 Reading: 9.1-9.9 Practice problems: those in assigned text and 29-35, 37-40 Substitution and Elimination Reactions of Alkyl Halides SUBSTITUTION REACTIONS Y + R X R Y + X Y takes the place of X (Substitution) Y “displaces” X One group takes the place of another.
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10/26/09 2 N u : - + R X R N u + :X - nucleophile substrate product leaving group NUCLEOPHILIC DISPLACEMENT The nucleophile “displaces” the leaving group. This is a “substitution” reaction: Nu substitutes for X (takes its place). NUCLEOPHILIC SUBSTITUTION Example 1 iodide displaces bromide at carbon NaI is soluble in acetone, NaCl and NaBr are not *
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10/26/09 3 Example 2 solvolysis of isopropyl chloride in water The extra proton is taken by a second water molecule. * water displaces chloride at carbon NUCLEOPHILIC SUBSTITUTION REACTIONS (substitution at carbon) ACID BASE REACTIONS (substitution at hydrogen) can be compared to … DISPLACEMENT REACTIONS
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10/26/09 4 COMPARE THESE REACTIONS N u : - + R X R N u + :X - nucleophile substrate product leaving group DISPLACEMENT AT CARBON base acid conjugate acid conjugate base :X - + B H H X + B : - DISPLACEMENT AT HYDROGEN
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10/26/09 5 R O R ' R ' C C R R ' C O O R NUCLEOPHILES A WIDE SELECTION OF NUCLEOPHILES MAKES POSSIBLE THE SYNTHESIS OF MANY TYPES OF ORGANIC COMPOUNDS: Nucleophile Product R X alkyl halides R O H alcohols ethers C N R nitriles esters alkynes R S H thiols Class R-Y + Nu R-Nu + Y R ' O - R ' N H R O R' R THE NUCLEOPHILE DOES NOT NEED TO BE CHARGED HOWEVER, REACTIVE ATOMS BEAR A LONE PAIR Nucleophile Product alcohols Class O H H O R H ethers O R H R N H 2 amines R ' N H 2 N H 3 amines O H H + R B r O H H R + + B r O H R O H H + H 3 O + + B r - - Under some circumstances water will react.
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