CHEM 210 [CHAPTER 6: SUBSTITUTION REACTIONS OF ALKYL HALIDES Addition Reactions of Alkenes Our text does not cover reaction 8 until a later chapter Additional Problems 1. Predict the products for the following reactions: 2. Propose a mechanism for the following: 1 Fall 2013 CHEM 210 [CHAPTER 6: SUBSTITUTION REACTIONS OF ALKYL HALIDES 3. Draw a mechanism for the following: 4. If an alcohol is used instead of water, ethers are produced. Draw a mechanism for the following: 5. Many reactions are intramolecular. Here the reactants are both in the same molecule. Draw a mechanism to explain the following: 6. Mercury is toxic and used only when necessary for synthesis. In class we learned that the oxy-‐ mercuration/demercuration scheme could be used to give products of alkene hydration without rearrangements. For each of the following reactions, give the product of each and indicate the product you would obtain by simple hydration in aqueous acid. 7. Complete the following examples of hydroboration/oxidation: 2 Fall 2013 CHEM 210 [CHAPTER 6: SUBSTITUTION REACTIONS OF ALKYL HALIDES 8. Complete the following examples of hydroboration/oxidation. Indicate proper stereochemistry of products. 9. Predict the products of the following catalytic hydrogenations. 10. Predict the products of the following halogenation reactions: 11. Predict the products when each alkene is treated with a mixture of water and Br2: 12. Bromonium ions can be captured by nucleophiles other than water. Predict the products of the following: 13. Predict the products; indicate proper stereochemistry where necessary: 3 Fall 2013 CHEM 210 [CHAPTER 6: SUBSTITUTION REACTIONS OF ALKYL HALIDES 14. Predict the products when each alkene is treated with O3 followed by Me2S: 15. Predict the products: 16. Predict the products: 4 Fall 2013 CHEM 210 [CHAPTER 6: SUBSTITUTION REACTIONS OF ALKYL HALIDES KEY 1. Predict the products for the following reactions: 2. Propose a mechanism for the following: 3. Draw a mechanism for the following: 4. 5 Fall 2013 CHEM 210 [CHAPTER 6: SUBSTITUTION REACTIONS OF ALKYL HALIDES 5. 6. 7. 6 Fall 2013 CHEM 210 [CHAPTER 6: SUBSTITUTION REACTIONS OF ALKYL HALIDES 8. 9. 7 Fall 2013 CHEM 210 [CHAPTER 6: SUBSTITUTION REACTIONS OF ALKYL HALIDES 10. 11. 12. 8 Fall 2013 CHEM 210 [CHAPTER 6: SUBSTITUTION REACTIONS OF ALKYL HALIDES 13. 9 Fall 2013 CHEM 210 [CHAPTER 6: SUBSTITUTION REACTIONS OF ALKYL HALIDES 14. 15. 10 Fall 2013 CHEM 210 [CHAPTER 6: SUBSTITUTION REACTIONS OF ALKYL HALIDES 16. 11 Fall 2013