7. Alkenes Reactions and Synthesis.ppt

McMurry Organic Chemistry 6th edition Chapter 7 (c) 2003 7. Alkenes: Reactions and Synthesis Based on McMurry’s Organic Chemistry, 6th edition Diverse Reactions of Alkenes Alkenes react with many electrophiles to give useful products by addition (often through special reagents) alcohols (add H-OH) alkanes (add H-H) halohydrins (add HO-X) dihalides (add X-X) halides (add H-X) diols (add HO-OH) cyclopropanes (add :CH2) 7.1 Preparation of Alkenes: A Preview of Elimination Reactions Alkenes are commonly made by elimination of HX from alkyl halide (dehydrohalogenation) Uses heat and KOH elimination of H-OH from an alcohol (dehydration) require strong acids (sulfuric acid, 50 oC) 7.2 Addition of Halogens to Alkenes Bromine and chlorine add to alkenes to give 1,2-dihaldes, an industrially important process F2 is too reactive and I2 does not add Cl2 reacts as Cl+ Cl- Br2 is similar Addition of Br2 to Cyclopentene Addition is exclusively trans Mechanism of Bromine Addition Br+ adds to an alkene producing a cyclic ion Bromonium ion, bromine shares charge with carbon Gives trans addition 7.3 Halohydrin Formation This is formally the addition of HO-X to an alkene (with +OH as the electrophile) to give a 1,2-halo alcohol, called a halohydrin The actual reagent is the dihalogen (Br2 or Cl2 in water or in an organic solvent) Mechanism of Formation of a Bromohydrin Br2 forms bromonium ion, then water adds Orientation toward stable C+ species Aromatic rings do not react An Alternative to Bromine Bromine is a difficult reagent to use for this reaction N-Bromosuccinimide (NBS) produces bromine in organic solvents and is a safer source 7.4 Addition of Water to Alkenes Hydration of an alkene is the addition of H-OH to to give an alcohol Acid catalysts are used in high temperature industrial processes: ethylene is converted to ethanol 7.7 Reduction of Alkenes: Hydrogenation Addition of H-H across C=C Reduction in general is addition of H2 or its equivalent Requires Pt or Pd as p