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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

prob E17.3c2 image

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SOLUTION E17.3c Bromide is a good nucleophile and a good leaving group, so substitution in dilute aqueous KBr solution can occur, primarily via S_N2 (secondary alkyl halide, no resonance) but S_N1 can also occur. Inversion of stereochemistry occurs with each S_N2 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).