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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 E21.1b 2

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SOLUTION E21.1b The second reaction is faster. The substrate is the same, but the leaving group is not. When alcohols are put in acidic solutions, the OH can be protonated to make a better leaving group (R-OH₂⁺ vs R-OH). In both E1 and E2 reactions, the type of leaving group affects the activation energy.
The first reaction is faster. The substrates, leaving group, and nucleophile are the same, but the solvent is different. Protic solvents better solubilize the carbocation and leaving group, improving both species’ stability. In E1 reactions, the stability of the carbocation affects the activation energy.