alkenes reactions
Post on 20-Nov-2015
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AlkenesAddition ReactionsSynthesis
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Addition of HBr or HClMarkovnikov Addition
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HBr Addition with RO-ORAnti-Markovnikov
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Free-Radical Mechanism
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Addition of Br2
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A Similar Mechanism to the Addition of HBr?
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Trans is formed exclusively(No cis is formed)
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Carbocation can be Stabilized by Neighboring Br
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Bromonium Ion is Opened Equally from Both Sides
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DefinitionsStereospecific only one stereoisomer is formed at the expense of the other (e.g. trans vs. cis)Stereoselective one stereoisomer is formed preferentially over the other.
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Anti-Addition Stereospecific ReactionAnti-addition
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Bromonium Ion Intermediate
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Halohydrins
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Bromohydrin FormationAddition of Br OHStereospecific & Regiospecific
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Unsymmetrical Bromonium ionH2O opens ring at more hindered site
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Br and OH are trans in anti addition
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Catalytic Hydrogenationsyn addition
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Mechanism Syn Addition
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Syn Addition of H2
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Hydrogenationall alkene p bonds are reduced
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Hydrogenated Vegetable Oil
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HydrationAddition of H2O
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Oxymercuration HydrationMarkovnikov additionRegiospecific Reaction
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Oxymercuration Mechanism
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Predict the Oxymercuration Hydration Products
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What Alkene would you use to Make These Alcohols?
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Hydroboration Hydration Anti-Markovnikov Syn addition
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BH3 adds to Alkene
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Hydroboration
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Regiochemistry is Anti-Markovnikov
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Syn Addition of H2O
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Draw the Major Products
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2 Complementary Hydration Reactions
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Oxymercuration the more highly substituted alcohol formsHydroboration the less highly substituted alcohol forms
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Predict Both Oxymercuration and Hydroboration Products
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Cyclopropanation
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A Carbene is Similar to Geometry of a Carbocation
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Dichlorocarbene Reactions
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Simmons-Smith Reaction
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In situ Preparation of Carbene
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Two MCAD Inhibitors
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Epoxide PreparationFrom Alkenes
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Epoxide PreparationFrom Halohydrins
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Mechanism
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Epoxide groups are Common in Biologically Active Molecules
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A New Class of Anti-tumor Agents
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Ozonolysis Forms 2 Carbonyl Compounds
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OzonolysisAlkene Cleavage
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Mechanism of Ozonolysis
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What Alkene will Undergo Ozonolysis to Give the Products Shown?
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Addition polymers
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Air Pollution Reacts with Tires
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O3 reacts with all alkene p Bonds
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Problem A symmetrical unknown compound A, C8H16, reacts with H2 on a 1% Pt/C catalyst to form B (C8H18). Treatment of A with O3 followed by Zn/HOAc affords butanone only. Identify A and B.
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