OrganicFallChpt6

OrganicFallChpt6 - Homework Chapter 6- All in chapter...

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Unformatted text preview: Homework Chapter 6- All in chapter problems- End of chapter: 22, 24, 28, 30, 32, 42, 52- Extra problems: Suggest synthesis for the following problems. Remember your target molecule is the first molecule! OH Br Br OH Reactions of alkenes Last chapter was formation of alkenes. This chapter is reactions of alkenes. Hydrogenation Reaction of alkenes with hydrogen gas Reduction reaction H = -136 kJ/mole Note that a catalyst is used. If not, you need about 30 atm of pressure and heat. Other catalysts are Pt, Ni, Rh Book says Pt is most used, but it is the most expensive Most catalysts do not dissolve in a solvent Heterogeneous reaction Heats of hydrogenation Same rules for stability More subtituted, less energy released during hydrogenation H H H H + H 2 Pd on C H H H H H H Easier to show relieved stress in cis systems than in trans systems Stereochemistry of hydrogen addition First step is always addition to catalyst Pi bond bonds with metal, allowing hydrogen to add Addition is called syn addition, as in the hydrogens add from the same side. The hydrogens add both cis or trans Opposite of this is anti addition, the same stereoselectivity as the elimination that occurs in the E2 reaction H H H H M H H H H H H H H COOH COOH H H COOH COOH COOH COOH H H + H 2 2 Pd on C Halide addition to alkenes Reaction Rates of reactivity HI > HBr > HCl >> HF Electrophilic addition General mechanism Markonikovs rule When an unsymmetrically substituted alkene reacts with a hydrogen halide, the hydrogen adds to the greater number of hydrogen substitutents and the halogen adds to the carbon having fewer substitutents Why is this true?...
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OrganicFallChpt6 - Homework Chapter 6- All in chapter...

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