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Topic+5+Notes+_acids+and+bases_ - L TOPIC 5 ORGANIC...

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TOPIC 5. ORGANIC REACTIONS: ACIDS AND BASES (Chapter 3) L
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OBJECTIVES 1. Classify types of reaction: -Addition, Substitution, Elimination, Rearrangement 2. Define the concept of “Mechanism” 3. Discuss the thermodynamics (equilibrium) and kinetics (rate) of organic reactions 4. Describe acid-base reactions 5. Develop relationships between structure and acidity/basicity 6. Take a first look at acid-promoted reactions
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Practical Aspects of Running a Reaction Starting material (“substrate”) Reagents Catalysis (lowers activation energy) Solvent (allows for mixing) Mode of addition BEGINNING Product Byproducts Unreacted reactants Catalyst Solvent SEPARATION PURIFICATION IDENTIFICATION END Time Temperature (heating/cooling) Environment (avoid O 2 , H 2 O?) Stirring % yield = moles of product moles of limiting reactant x 100
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Representations of reactions ...more commonly written as….
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CLASSIFYING REACTIONS Reactions are conveniently classified as substitutions, additions, eliminations and rearrangements. These terms describe the overall process, simply comparing the structure of starting materials and products. They do not indicate anything about the pathway (“mechanism”) by which the reaction proceeds. Substitutions Additions Eliminations Rearrangements (often in combination with another type of reaction) S:3.1
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Substitution
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Addition
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Elimination
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Rearrangement
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A Preview of Reactivity
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In Class Problem: Designate each of the following reac1ons as (a) a subs1tu1on, (b) an elimina1on, (c) an addi1on, (d) a rearrangement, or (e) some combina1on of the former.
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WHAT IS A MECHANISM? A mechanism is a proposal for a step-by-step pathway by which a reaction proceeds. Each step involves bond making and/or breaking. The mechanism takes into account all currently available evidence (kinetics, formation of byproducts, effect of structure on reactivity). Any new data collected must be consistent with the proposed mechanism, or the mechanism itself must be modified to account for the new finding. An understanding of common mechanistic steps can be applied to new combinations of reagents to predict the outcome of a new reaction. As such, development of an understanding of mechanisms will save you from memorizing a huge amount of material. While you must develop a familiarity with reactions, do not try to pass this course by just memorizing the outcome of reactions!
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Electrophiles and Nucleophiles Nucleophile Electron-rich, “nucleus-loving” species Electrophile Electron-deficient, “electron-loving” species seek a proton or some other positively charged center Representation: Nu or Nuc (if neutral) or Nu or Nuc (if anionic) seek electrons to obtain a stable valence shell of electrons Representation: E or El
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The Use of Curved Arrows in Illustra6ng Reac6ons Curved arrows show the flow of electrons in a reac1on and not the movement of atoms.
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