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 E18.1a

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The second reaction is faster. Substrate is the same, but CH3SH is the better nucleophile (both neutral, S less electronegative and larger/more polarizable). In SN2 reactions, strength of nucleophile affects the activation energy.

The second reaction is faster. Substrate and nucleophile are the same, but concentration of nucleophile is greater in the second (twice as much, so twice as fast). In SN2 reactions, concentration of nucleophile affects the rate as it is part of the rate equation.
 

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