Chem357_Sub_Elim__FINAL_Student_

Chem357_Sub_Elim__FINAL_Student_ - Substitution &...

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1 Substitution & Elimination Substitution & Elimination Unit 1 - S Unit 1 - S N 2 Paula Y. Paula Y. Bruice Bruice , , Chapter 8 & 9 Chapter 8 & 9 2 Nucleophilic Substitution and Elimination Reactions Substitution and Elimination Reactions This next set of lectures is extremely important This is the real beginning of building molecules - up until now, we have simply modified structures by adding other small molecules (e.g. H-X, H 2 O, X 2 , etc.). - we will start to build new molecules by forming new carbon-carbon bonds. Some students have considerable difficulty with the material….
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3 WARNING: This material will require you to pull together many fundamentals to assess the reaction outcomes. We strongly recommend that you go back through your notes and problem sets and review these concepts to prepare. ( e.g. acid-base chemistry, nucleophiles and electrophiles, electron-pushing mechanisms, steric effects, carbocation stability and rearrangements, etc.) Nucleophilic Nucleophilic Substitution and Elimination Reactions Substitution and Elimination Reactions 4 Nucleophilic Substitution and Elimination Reactions Substitution and Elimination Reactions S e a h a r e s are large marine shell-less gastropod molluscs in the family Aplysiidae (suborder Anaspidea, subclass Orthogastropoda, class Gastropoda, phylum Mollusca).
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5 Nucleophilic Nucleophilic Substitution and Elimination Reactions Substitution and Elimination Reactions 6 Nucleophilic Substitution and Elimination Reactions Substitution and Elimination Reactions C C X H + Nuc C C Nuc H X + Substitution Rxn X = Leaving group Let us consider the following scenario: but we also see….
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7 Nucleophilic Nucleophilic Substitution and Elimination Reactions Substitution and Elimination Reactions C C X H + Nuc C C + X H-Nuc Elimination Rxn … different products resulting from a different reaction pathway. 8 Nucleophilic Substitution and Elimination Reactions Substitution and Elimination Reactions C C X H + Nuc C C Nuc H X + Substitution Rxn C C + X H-Nuc Elimination Rxn R e a c t i o n p h w y s l d g u b m r A L W Y S . f
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9 S N 2 - 2 - Nucleophilic Nucleophilic Substitution Bimolecular Substitution Bimolecular The S N 2 Reaction Br D T H + Cl D T H Br + Cl 10 4.0 x 10 -3 0.40 M 0.40 M 3.0 x 10 -3 0.60 M 0.20 M 2.0 x 10 -3 0.40 M 0.20 M 3.0 x 10 -3 0.20 M 0.60 M 2.0 x 10 -3 0.20 M 0.40 M 1.0 x 10 -3 0.20 M 0.20 M Rate (M/s -1 ) [ alkylBr ] (M) [ Cl ] (M) Br D T H + Cl D T H Br + Cl nucleophile electrophile ! " ! + G e n e r a l R a t e L a w RATE = k [alkylBr] x [Cl ] y S N 2 - 2 - Nucleophilic Nucleophilic Substitution Bimolecular
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11 S N 2 - 2 - Nucleophilic Nucleophilic Substitution Bimolecular Substitution Bimolecular The S N 2 Reaction Br D T H + Cl D T H Br + Cl 12 S N 2 - 2 - Nucleophilic Nucleophilic Substitution Bimolecular Br D T H Cl S.M. Products Cl D T H Br ! G Reaction Coordinate Transition state c o n e r t d - s p i m a S N 2
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13 S N 2 - 2 - Nucleophilic Nucleophilic Substitution Bimolecular Substitution Bimolecular !
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This note was uploaded on 03/29/2009 for the course CHEM 3570 taught by Professor Ganem, b during the Fall '06 term at Cornell University (Engineering School).

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Chem357_Sub_Elim__FINAL_Student_ - Substitution &...

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