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225Sp10 Topics for Test _5 - c The reaction solvent B...

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CHEMISTRY 225, SPRING 2010 TOPICS FOR TEST #5, JUNE 18, 2010 U N I T V I : R E A C T I O N S O F A L K Y L H A K I D E S I. Fundamental Principles of Organic Reactivity A. Thermochemical analysis of organic reactions 1. Kinetics 2. Thermodynamics 3. Determination of H from bond energies 4. The transition state 5. Multistep reactions B. Acids and bases revisited 1. Acid-base properties of amines, alcohols 2. Lewis acids and bases 3. “Frontier orbital” analysis II. Bimolecular Substitution with Alkyl Halides A. The S N 2 reaction 1. Alkyl halides: structure and reactivity 2. General aspects of the S N 2 reaction 3. The nucleophile a. Examples: the range of nucleophiles b. Relative nucleophilicity 4. The electrophile a. Reactivity order in the S N 2 reaction b. Electrophiles other than alkyl halides
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Unformatted text preview: c. The reaction solvent B. Mechanism of the S N 2 reaction 1. Kinetics and stereochemistry 2. The transition state for the S N 2 reaction a. Backside displacement b. Maximum orbital overlap 3. The Hammond Postulate [recitation, 6/16/10] 4. Chemical implications of inversion of configuration C. The S N 2 reaction for synthesis III. Unimolecular Reactions of Alkyl Halides A. The S N 1 reaction 1. Experimental data: kinetics and stereochemistry 2. Mechanism of the S N 1 reaction B. Carbocations 1. Carbocations in the S N 1 reaction 2. Properties and stabilities of carbocations TEXTBOOK REFERENCES: Sec. 6.2 – 6.4, Sec. 6.7c; Sec 7.1 – 7.7, 7.10; Sec. 8.1 – 8.8 COURSEPACK PAGES: 39 – 46...
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