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 E17.3c

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Bromide is a good nucleophile and a good leaving group, so substitution in dilute aqueous KBr solution can occur, primarily via SN2 (secondary alkyl halide, no resonance) but SN1 can also occur. Inversion of stereochemistry occurs with each SN2 reaction leading to mixtures of stereoisomers.
Hydroxide (-OH) is a good nucleophile but a bad leaving group, so substitution does not occur at all with 2-butanol in OH (aq) (substitution of alcohols only occurs in acidic solution to protonate and make a better “H2O” leaving group).

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