CHEM 2211 1st Edition Lecture 19 Outline of Last LectureI. Addition of water to alkenesII. Addition of alcohol to alkenesIII. 1,2 hydride shifIV. Methyl shifOutline of Current LectureI. Summary of reaction mechanismsCurrent LectureI. Summary of reaction mechanismsA. Drawingi. Curvy arrows always pushes electrons from the nucleophile to the electron deficient electrophileii. Because pi bonds are weaker than sigma bonds, they are the bond most likely to be brokenB. Hydration reactionsi. Also known as acid catalyzed hydration (acid is usually H2SO4)ii. Final product: and ALCOHOLC. Addition of Alcohol to Alkenesi. Also requires and acid catalyst (usually H2SO4)ii. Final product: ETHERD. Carbocation rearrangementi. 1,2 Hydride Shif1. Movement of a hydride ion (H-) to stabilize the molecule2. Rules:a. Hydride only moves if movement will stabilize the molecule moreb. Only happens once in the course of a reaction3. Final product: MORE stable carbocationii. Methyl Shif1. Exactly like a hydride shif but involves the movement of a methyl group instead2. Final product: MORE stable carbocationE. Halogenation of an alkenei. “Bridging” between the carbons on the double bondii. Final product: a DIhalogen alkaneiii. Type of addition: ANTIF. Halohydrin formationi. Halogenation in the presence of waterii. Final Product: an ALCOHOL with ONE halogen attachediii. Type of addition: ANTIG. Hydroboration-Oxidationi. Manipulates the regioselectivity experienced by moleculesii. An ANTI-Markovnikov reactioniii. Final Product: ALCOHOLiv. Type of addition:
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