11-03 - Give a synthesis of the following alcohol Use...

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11/3/2010 1 Give a synthesis of the following alcohol: Use electrophilic addition to an alkene as the last step . Start with any compound with four carbons or less. Use any inorganic reagents you need. You will need more than one reaction. Which of these routes is best? A H H NaNH 2 Br H 2 Pd 1. Hg(OAc) 2 2. BH 4 - 33 B C D CH 3 H NaNH 2 Br Na NH 3 H H NaNH 2 Br H 2 Lindlar CH 3 H NaNH 2 Br 1. Hg(OAc) 2 2. BH 4 - H 2 O H 2 SO 4 H 2 O H 2 SO 4 H 2 Lindlar CH 3 H H H H Br HBr Regiochemistry? Alkene Addition Reactions 34 Oxymercuration and acid-catalyzed hydration have the same regiochemistry . Synthesis of Alcohols from Alkenes 35 But what if you want the primary alcohol? How do you switch the regioselectivity? An acid will add to the less-substituted carbon… …to make the more stable 2° carbocation 36 Boron can form stable bonds with carbon Tricoordinate Boron compounds are Lewis Acids. Can Boron-containing compounds add to alkenes?
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