ALKENES AND ALKYNES II' OXIDATION AND REDUCTION OXYMERCURATION AND HYDROBORATION SIMPLE RING FORMATI

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ALKENES AND ALKYNES II.OXIDATION AND
REDUCTIONOXYMERCURATION ANDHYDROBORATIONSIMPL
E RING FORMATION

• Chapter 14

Chapter 14
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Assignment for Chapter Fourteen

• DO Special Topics box after page 14-1
• DO Sections 14.0 - 14.2
• READ Section 14.3
• DO Section 14.4
• DO Sections 14.5 - 14.11
• DO Section 14.12 (lightly)
• READ Section 14.13
• DO Summary and Problems

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Problem Assignment

• In-Text Problems
• 14-1 through 14-20
• End-of-Chapter Problems
• 25 through 34
• 35 through 40
• 43, 45, 46, 47, 49, 50

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What is Oxidation?

• Gain of oxygen atoms
• Loss of hydrogen atoms

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What is Reduction?

• Gain of hydrogen atoms
• Loss of oxygen atoms

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anti-Glycol Formation
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Mechanism of anti-Glycol Formation
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Epoxide Intermediate
Sterically hindered
Underside not hindered
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anti-Glycol Formation from cis-2-Butene
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syn-Glycol Formation (I)
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Cyclic Osmate Intermediate
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syn-Glycol Formation (II)
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syn-Glycol Formation fromcis-2-Butene
could also use KMnO4
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Ozonolysis
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Hydrogenation of Alkenes
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Hydrogenation of Alkynes
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Lindlar Method
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Dissolving Metal Reduction
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The dissolving metal reduction is chemospecific
-- It does not affect double bonds.
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In Summary

• Lindlar Method
• Sodium in Liquid Ammonia Method