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 – Markonikov’s 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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This note was uploaded on 03/27/2008 for the course CHEM 3630 taught by Professor Ruane during the Spring '07 term at Wisc Platteville.

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OrganicFallChpt6 - Homework Chapter 6 All in chapter...

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