Lecture_13 - Lecture 13 Chapter 4: Alkene Reac5vity...

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Unformatted text preview: Lecture 13 Chapter 4: Alkene Reac5vity Rearrangement of Carboca5ons  1,2 ­Hydride shi. or 1,2 methyl shi. can occur –  Consider HBr addi9on to 3,3 ­dimethyl ­1 ­butene Rearrangement of Carboca5ons  1,3 ­shi.s do not usually occur  Rearrangement must lead to more stable C+  Rearrangements can lead to ring expansions Ques5on?  Which of the products are not likely formed? Ques5on?  Which of the products are not likely formed? Addi5on of Halogens to Alkenes  Dihalogen bonds are rela9vely weak, so they can be electrophiles –  Bromina9on How Do We Know It’s a Bromonium? Halohydrin Forma5on  What if you do the previous rxn in water? Regioselec5vity of Nucleophile  Chlorina9on of 2 ­methyl ­2 ­butene in presence of methanol Other Ways to add Water to an Alkene  Oxymercura9on ­reduc9on –  No acid, no carboca9on, no rearrangement Mechanism ...
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This note was uploaded on 09/09/2011 for the course CHEM 109A taught by Professor Bruice during the Spring '07 term at UCSB.

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