Alkenes and Alkynes - URI Department of Chemistry

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10/29/2010Orientation of Electrophilic Addition:Markovnikov’s Rule (Restated)Worked Example 7.2Predicting the Product of an Electrophilic AdditionReactionWhat product would you expect from reaction of HClwith 1-ethylcyclopentene?Worked Example 7.3Synthesizing a Specific CompoundWhat alkene would you start with to prepare thefollowing alkyl halide?(There may be more than one possibility.)8
10/29/20107.8 Carbocation Structure and StabilityWhy Markovnikov’s Rule worksStructure of carbocations• Carbocations are planar• The trivalent carbon is sp 2hybridized and has a vacant porbital perpendicular to theplane of the carbon• Carbon has three attachedgroupsCarbocation Structure and StabilityStability• Thermodynamic measurements show that the stability ofcarbocations increases with increasing substitution.Carbocation Structure and Stability• More highly substituted carbocations are more stablethan less highly substituted ones• Inductive effect• The more alkyl groups that are attached to the positivelycharged carbon, the more electron density shifts toward thecharge and the more inductive stabilization of the cationoccurs9
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