week 1 - 5 - Chemistry S-20ab Chemistry E-2a: Lecture 4...

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Addition of X 2 with Water or Alcohols If Br 2 or Cl 2 is added to an alkene in the presence of water (HOH) or an alcohol (ROH), a different product is formed. Can you propose a mechanism for this reaction? + Br 2 + H 2 O Br OH Now that you’ve seen the mechanism, can you predict which of the following products will be produced in the reaction of cyclohexene with bromine in water? OH Br Br 2 H 2 O OH Br or Reading : Section 5.1 Chemistry S-20ab Week 1 66
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Chemistry S-20ab Week 1 67 The Structure of the Bromonium Ion Explain why only one product is observed in the following reaction: Br 2 H 2 O HO Br Is this observation consistent with Markovnikov’s Rule? Why or why not? Given all that you know about the addition of Br 2 to alkenes, predict which of the four products shown below would be the main product observed in the addition of bromine to 1-methylcyclohexene in the presence of water: Br 2 H 2 O Br OH Br OH Br OH OH Br A B C D Reading : Section 5.1
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Review of Alkene Hydration You already know one method for accomplishing the following transformation. What is that method? What is its mechanism? OH Now suppose you want to carry out the following transformation. Can you use the same method as you did above? Why or why not? OH What kinds of reactions might we want to avoid when carrying out organic synthesis in the laboratory? Reading
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This note was uploaded on 07/21/2010 for the course CHEM S20ab taught by Professor Mccarty during the Summer '10 term at Harvard.

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week 1 - 5 - Chemistry S-20ab Chemistry E-2a: Lecture 4...

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