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Organic Chemistry Main Menu Lecture 1: Introduction to Molecular Orbitals Lecture 10: Intermolecular Forces and Intro to Reactivity Lecture 11: Alkenes as Nucleophiles I Lectures 12 and 13: Alkenes II & III Lecture 14: Benzenes as Nucleophiles I Lecture 15 objectives and skills Lecture 2: Molecular Orbitals in Organic Structures Lecture 3: Molecular Orbitals and Resonance Lecture 4: Molecular Orbitals and Aromaticity Lecture 5: Nomenclature and IR Spectroscopy Lecture 6: Stereochemistry I Lecture 7: Stereochemistry II Lecture 8: Newman and Fisher Projections Lecture 9: Conformations and Cyclohexane Rings

SOLUTION 18.1b 2

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SOLUTION 18.1b The first reaction is faster. The substrate substitution is the same, but iodide is the better leaving group over chloride. I- is larger and the weaker base (more stable anion). In both S_N1 and S_N2 reactions, the type of leaving group affects the activation energy.

Debatable that they are approximately the same rate. In both cases, the protic solvent is the nucleophile (solvolysis). The identity of the protic solvent is the only difference between the two reactions. Since the strength and concentration of nucleophile do not affect the rate of S_N1 reactions, they should proceed at the same rate. A slight difference in rate may come from the solvent effects. Water is the more polar of the two solvents, which could stabilize the carbocation enough MORE than methanol to increase reaction rate in water.