Lecture04outline

Lecture04outline - I Review The relevant molecular orbital...

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I. Review • The relevant molecular orbital for anions (or any nucleophile or base) is the HOMO, and the HOMO of the allyl anion shows that reactivity occurs at the termini • Allyl anions are nucleophiles that contain a functional group, making them quite useful for synthesis • Allylic halides are unusually reactive in S N 2 reactions due to the interaction of the electrons from the π -bond of the alkene with σ * of the C–X bond • S N 2' reactions, in which nucleophiles react at an alkenyl carbon, followed by alkene transposition and leaving group extrusion, are also possible for allylic halides though are not major pathways unless the S N 2 option is sterically prohibited • Alkenes and dienes react in a cycloaddition reaction to form cyclohexenes, but dienes do not dimerize to form cyclooctadienes • Both processes proceed through the same type of mechanism and are strongly favored enthalpically due to a the conversion of π -bonds to σ -bonds, though are slightly unfavorable entropically because of the conversion of two particles to one
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This note was uploaded on 05/17/2010 for the course CHEM 0740 taught by Professor Professor during the Spring '10 term at Pittsburgh.

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Lecture04outline - I Review The relevant molecular orbital...

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