Lecture_12 - Lecture 12 Chapter 4: Alkene Reac5vity...

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Unformatted text preview: Lecture 12 Chapter 4: Alkene Reac5vity Regioselec5vity  Regioselec5vity is the preference for one cons-tu-onal isomer over the other –  Addi-on of HCl to propene –  Addi-on of HCl to 1 ­methylcyclopentene Markovnikov’s Rule  Electrophile adds to sp2 Carbon with most H’s –  Addi-on of HBr to 2 ­pentene: –  Addi-on of HBr to 1 ­butene Planning a Synthesis (Retrosynthesis)   Let’s say you want to make 3 ­bromohexane, which alkene do you use? Acid ­Catalyzed Addi5on Reac5on  Hydra-on of 1 ­propene Acid ­Catalyzed Addi5on Reac5ons  Synthesis of ethers –  Acid catalyzed addi-on of methanol to 1 ­propene Retrosynthesis of Alcohols and Ethers  Indicate reactants and catalyst to give product –  1 ­methoxycyclohexane –  2 ­ethoxybutane Carboca5ons Can Rearrange  Some-mes the product doesn’t appear to follow Markovnikov’s rule. –  Addi-on of HBr to 3 ­methyl ­1 ­butene ...
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